Substituted pyridyl keto enols

ABSTRACT

The invention relates to new pyridyl-substituted cyclic ketoenols of the formula (I) ##STR1## in which V 1 , V 2  or V 3  represents nitrogen, 
     Het represents one of the groups ##STR2## A, B, G, W, Z and z have the meanings given in the description, to a plurality of processes and intermediates for their preparation, and to their use as pesticides and herbicides.

The invention relates to new pyridyl-substituted cyclic ketoenols, to aplurality of processes and intermediates for their preparation, and totheir use as pesticides and herbicides.

No pyridyl-substituted heterocyclic ketoenols have been described todate. What is known is that certain phenyl-substituted cyclic ketoenolsare insecticidally, acaricidally and/or herbicidally active.

Unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives(EP-A-355 599 and EP-A-415 211) and substituted monocyclic3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077)which have a herbicidal, insecticidal or acaricidal action have beendisclosed.

Furthermore, polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A442 073) and 1H-arylpyrrolidinedione derivatives (EP-A-456 063, EP-A-521334, EP-A-596 298, EP-A-613 884, EP-A-613 885, DE 44 40 594, WO 94/01997, WO 95/01 358, WO 95/20 572, EP-A-668 267 and WO 95/26 954) havebeen disclosed.

It has been disclosed that certain substituted Δ³ -dihydrofuran-2-onederivatives have herbicidal properties (cf. DE-A-4 014 420). Thesynthesis of the tetronic acid derivatives used as starting compounds(such as, for example,3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-Δ³ dihydrofuran-2-one)is also described in DE-A-4 014 420. Furthermore, 3-aryl-Δ³-dihydrofuranone derivatives which have herbicidal, acaricidal andinsecticidal properties have been disclosed in EP-A-528 156 and EP-A-0647 637. 3-Aryl-Δ³ -dihydrothiophenone derivatives have also beendisclosed (WO 95/26 345).

Phenyl-pyrone derivatives substituted in the phenyl ring which haveherbicidal, acaricidal and insecticidal properties are described inEP-A-588 137.

5-Phenyl-1,3-thiazine derivatives substituted in the phenyl ring whichhave herbicidal, acaricidal and insecticidal action have been describedin WO 94/14 785.

However, the herbicidal, acaricidal and insecticidal activity and/orspectrum of action, and the plant tolerance of these compounds, inparticular by crop plants, is not always sufficient.

There have now been found new compounds of the formula (I) ##STR3## inwhich

A) V¹ represents nitrogen and

V² represents CH or C--Z and

V³ represents CY or

B) V¹ represents CX and

V² represents nitrogen and

V³ represents CY or

C) V¹ represents CX and

V² represents CH or C--Z and

V³ represents nitrogen

and in which

W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkinyl,alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, orin each case optionally substituted phenyl, phenoxy, phenylthio,phenylalkoxy or phenylalkylthio,

X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy,alkylthio, halo-genoalkyl, halogenoalkoxy, halogenoalkenyloxy, cyano,nitro or in each case optionally substituted phenyl, phenoxy,phenylthio, phenylalkyloxy or phenylalkylthio,

Y represents hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl,halo-genoalkoxy, cyano or nitro,

Z represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl,halogenoalkoxy, hydroxyl, cyano, nitro or in each case optionallysubstituted phenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or

Y and Z together with the carbon atoms to which they are bondedrepresent an optionally substituted cycle which is optionallyinterrupted by hetero atoms, in which case n represents 1, or

W and Z together with the immediately adjacent carbon atoms to whichthey are bonded represent an optionally substituted cycle which isoptionally interrupted by hetero atoms, in which case n represents 1,

n represents 0, 1 or, in the cases A) and C) also 2, it being possiblefor the substituents Z to be identical or different when n=2,

Het represents one of the groups ##STR4## in which

A represents hydrogen, or represents alkyl, alkenyl, alkoxyalkyl,polyalkoxyalkyl or alkylthioalkyl, each of which is optionallysubstituted by halogen, or represents in each case saturated orunsaturated and optionally substituted cycloalkyl or heterocyclyl, orrepresents aryl, arylalkyl or hetaryl, each of which is optionallysubstituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy,cyano or nitro,

B represents hydrogen, alkyl or alkoxyalkyl, or

A and B together with the carbon atom to which they are bonded representa saturated or unsaturated, optionally substituted carbocycle orheterocycle,

D represents hydrogen or an optionally substituted radical from theseries consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl,polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl,saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl orhetaryl, or

A and D together with the atoms to which they are bonded represent an ineach case optionally substituted carbocycle or heterocycle,

G represents hydrogen (a) or one of the groups ##STR5## in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R¹ represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl orpolyalkoxyalkyl, each of which is optionally substituted by halogen, orrepresents cycloalkyl or heterocyclyl, each of which is optionallysubstituted by halogen, alkyl or alkoxy, or represents in each caseoptionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl,

R² represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each ofwhich is optionally substituted by halogen, or represents in each caseoptionally substituted cycloalkyl, phenyl or benzyl,

R³, R⁴ and R⁵ independently of one another represent alkyl, alkoxy,alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, eachof which is optionally substituted by halogen, or represent in each caseoptionally substituted phenyl, benzyl, phenoxy or phenylthio,

R⁶ and R⁷ independently of one another represent hydrogen, or representalkyl cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, each of which isoptionally substituted by halogen, or represent in each case optionallysubstituted phenyl or benzyl, or together with the N atom to which theyare bonded form an optionally substituted cycle which optionallycontains oxygen or sulphur.

Depending on the nature of the substituents, the compounds of theformula (I) may also be present in the form of geometric and/or opticalisomers or variously composed isomer mixtures which, if appropriate, maybe separated in the customary manner. The present invention relates toboth the pure isomers and the isomer mixtures, to their preparation anduse, and to compositions comprising them. In the text which follows,however, compounds of the formula (I) will always be mentioned for thesake of simplicity, even though this is to be understood as meaning thepure compounds or, if appropriate, mixtures comprising various amountsof isomeric compounds.

Depending on whether V¹, V² or V³ represents nitrogen, the compounds ofthe formula (I) are compounds of the formulae (I-A), (I-B) or (I-C):##STR6## in which

Het, X, Y, Z, W and n have the abovementioned meanings.

To show the position of the pyridyl ring which is occupied by thenitrogen, the text below will occasionally use the letters (A), (B) or(C) when referring to formulae, and also precursors or intermediates.

Taking into consideration the meanings (1) to (5) of the group Het, thefollowing main structures (I-1) to (I-5) result: ##STR7## in which

A, B, D, G, W, V¹, V², V³, Z and n have the abovementioned meanings.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-1-a) to (I-1-g)result if Het represents the group (1), ##STR8## in which

A, B, E, L, M, W, V¹, V², V³, n, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ havethe abovementioned meanings.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-2-a) to (I-2-g)result if Het represents the group (2): ##STR9## in which

A, B, E, L, M, W, V¹, V², V³, n, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ havethe abovementioned meanings.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-3-a) to (I-3-g)result if Het represents the group (3): ##STR10## in which

A, B, E, L, M, W, V¹, V², V³, n, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ havethe abovementioned meanings.

Depending on the position of the substituent G, the compounds of theformula (I-4) may be present in the two isomeric forms of the formulae(I-4)_(a) and (I-4)_(b) ##STR11## which shall be expressed by the brokenline in formula (I-4).

The compounds of the formulae (I-4)_(a) and (I-4)_(b) may be present asmixtures, but also in the form of their pure isomers. If desired,mixtures of the compounds of the formulae (I-4)_(a) and (I-4)_(b) may beseparated by physical methods in a manner known per se, for example bychromatographic methods.

For reasons of clarity, in each case only one of the isomers which arepossible will be mentioned in the following text. This does not excludethat, if appropriate, the compounds can be present in the form of theisomer mixtures or in the respective other isomeric form.

Taking, into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following, main structures (I-4-a) to(I-4-g) result if Het represents the group (4): ##STR12## in which

A, D, E, L, M, W, V¹, V², V³, n, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ havethe abovementioned meanings.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-5-a) to (I-5-g)result if Het represents the group (5): ##STR13## in which

A, E, L, M, W, V¹, V², V³, n, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have theabovementioned meanings.

Furthermore, it has been found that the new compounds of the formula (I)are obtained by the processes described hereinbelow:

(A) Compounds of the formula (I-1-a) ##STR14## in which

A, B, W, V¹, V², V³, n and Z have the abovementioned meanings areobtained when compounds of the formula (II) ##STR15## in which

A, B, W, V¹, V², V³, n and Z have the abovementioned meanings and

R⁸ represents alkyl (preferably C₁ -C₆ -alkyl) are subjected to anintramolecular condensation reaction in the presence of a diluent and inthe presence of a base.

(B) Furthermore, it has been found that compounds of the formula (I-2-a)##STR16## in which

A, B, W, V¹, V², V³, n and Z have the abovementioned meanings areobtained when compounds of the formula (III) ##STR17## in which

A, B, W, V¹, V², V³, n, Z and R⁸ have the abovementioned meanings aresubjected to an intramolecular condensation reaction in the presence ofa diluent and in the presence of a base.

(C) Moreover, it has been found that compounds of the formula (I-3-a)##STR18## in which

A, B, W, V¹, V², V³, n and Z have the abovementioned meanings areobtained when compounds of the formula (IV) ##STR19## in which

A, B, W, V¹, V², V³, n, Z and R⁸ have the abovementioned meanings and

T represents hydrogen, halogen, alkyl (preferably C₁ -C₆ -alkyl) oralkoxy (preferably C₁ -C₈ -alkoxy) are subjected to an intramolecularcyclization reaction, if appropriate in the presence of a diluent and inthe presence of an acid.

(D) Moreover, it has been found that the compounds of the formula(I-4-a) ##STR20## in which

A, D, W, V¹, V², V³, n and Z have the abovementioned meanings areobtained when compounds of the formula (V) ##STR21## in which

A and D have the abovementioned meanings or their silyl enol ethers ofthe formula (Va) ##STR22## in which

A and D have the abovementioned meanings and

R^(8') represents alkyl (preferably methyl) are reacted with compoundsof the formula (VI) ##STR23## in which

W, V¹, V², V³, n and Z have the abovementioned meanings and Halrepresents halogen (preferably chlorine or bromine), if appropriate inthe presence of a diluent and if appropriate in the presence of an acidacceptor.

(E) Moreover, it has been found that the compounds of the formula(I-5-a) ##STR24## in which

A, W, V¹, V², V³, n and Z have the abovementioned meanings are obtainedwhen compounds of the formula (VII) ##STR25## in which

A has the abovementioned meaning are reacted with compounds of theformula (VI) ##STR26## in which

Hal, W, V¹, V², V³, n and Z have the abovementioned meanings, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid acceptor.

Furthermore, it has been found

(F) that the compounds of the formulae (I-1-b) to (I-5-b) shown above inwhich A, B, D, R¹, W, V¹, V², V³, n and Z have the abovementionedmeanings are obtained when compounds of the formulae (I-1-a) to (I-5-a)shown above in which A, B, D, W, V¹, V², V³, n and Z have theabovementioned meanings

α) are reacted with acid halides of the formula (VIII) ##STR27## inwhich

R¹ has the abovementioned meaning and Hal represents halogen (inparticular chlorine or bromine) or

β) are reacted with carboxylic anhydrides of the formula (IX)

    R.sup.1 --CO--O--CO--R.sup.1                               (IX)

in which

R¹ has the abovementioned meaning, if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent;

(G) that the compounds of the formulae (I-1-c) to (I-5-c) shown above inwhich A, B, D, R², W, M, V¹, V², V³, n and Z have the abovementionedmeanings and L represents oxygen are obtained when compounds of theformulae (I-1-a) to (I-5-a) shown above in which A, B, D, W, V¹, V², V³,n and Z have the abovementioned meanings are reacted in each case withchloroformic esters or chloroformic thioesters of the formula (X)

    R.sup.2 --M--CO--Cl                                        (X)

in which

R² and M have the abovementioned meanings, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent;

(H) that compounds of the formulae (I-1-c) to (I-5-c) shown above inwhich A, B, D, R², W, M, V¹, V², V³, n and Z have the abovementionedmeanings and L represents sulphur are obtained when compounds of theformulae (I-1-a) to (I-5-a) shown above in which A, B, D, W, V¹, V², V³,n and Z have the abovementioned meanings are reacted in each case

α) with chloromonothioformic esters or chlorodithioformic esters of theformula (XI) ##STR28## in which

M and R² have the abovementioned meanings, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent, or

β) with carbon disulphide and subsequently with compounds of the formula(XII)

    R.sup.2 -Hal                                               (XII)

in which

R² has the abovementioned meaning and Hal represents chlorine, bromineor iodine, if appropriate in the presence of a diluent and ifappropriate in the presence of a base;

(I) that compounds of the formulae (I-1-d) to (I-5-d) shown above inwhich A, B, D, R³, W, V¹, V², V³, n and Z have the abovementionedmeanings are obtained when compounds of the formulae (I-1-a) to (I-5-a)shown above in which A, B, D, W, V¹, V², V³, n and Z have theabovementioned meanings are reacted in each case with sulphonylchlorides of the formula (XIII)

    R.sup.3 --SO.sub.2 --Cl                                    (XIII)

in which

R³ has the abovementioned meaning, if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent;

(J) that compounds of the formulae (I-1-e) to (I-5-e) shown above inwhich A, B, D, L, R⁴, R⁵, W, V¹, V², V³, n and Z have the abovementionedmeanings are obtained when compounds of the formulae (I-1-a) to (I-5-a)shown above in which A, B, D, W, V¹, V², V³, n and Z have theabovementioned meanings are reacted in each case with phosphoruscompounds of the formula (XIV) ##STR29## in which

L, R⁴ and R⁵ have the abovementioned meanings and Hal represents halogen(in particular chlorine or bromine), if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent;

(K) that compounds of the formulae (I-1-f) to (I-5-f) shown above inwhich A, B, D, E, W, V¹, V², V³, n and Z have the abovementionedmeanings are obtained when compounds of the formulae (I-1-a) to (I-5-a)in which A, B, D, W, V¹, V², V³, n and Z have the abovementionedmeanings are reacted in each case with metal compounds or with amines ofthe formulae (XV) or (XVI) ##STR30## in which

Me represents a mono- or divalent metal (preferably an alkali metal oralkaline earth metal, such as lithium, sodium, potassium, magnesium orcalcium),

t represents the number 1 or 2 and

R¹⁰, R¹¹ and R¹² independently of one another represent hydrogen oralkyl (preferably C₁ -C₈ -alkyl), if appropriate in the presence of adiluent;

(L) that compounds of the formulae (I-1-g) to (I-5-g) shown above inwhich A, B, D, L, R⁶, R⁷, W, V¹, V², V³, n and Z have the abovementionedmeanings are obtained when compounds of the formulae (I-1-a) to (I-5-a)shown above in which A, B, D, W, V¹, V², V³, n and Z have theabovementioned meanings are reacted in each case with isocyanates orisothiocyanates of the formula (XVII)

    R.sup.6 --N═C═L                                    (XVII)

in which

R⁶ and L have the abovementioned meanings, if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or

β) with carbamoyl chlorides or thiocarbamoyl chlorides of the formula(XVIII) ##STR31## in which

L, R⁶ and R⁷ have the abovementioned meanings, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.

Moreover, it has been found that the new compounds of the formula (I)have a very good activity as pesticides, preferably as insecticides,acaricides and herbicides, and are in some cases additionally very welltolerated by plants, in particular crop plants.

The formulae (I) and (I-A), (I-B) and (I-C), respectively, providegeneral definitions of the compounds according to the invention.Preferred substituents or ranges of the radicals listed in the formulaementioned hereinabove and hereinbelow are illustrated in the followingtext:

W preferably represents hydrogen, nitro, cyano, halogen, C₁ -C₆ -alkyl,C₂ -C₆ -alkenyl, C₂ -C₆ -alkinyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁-C₄ -halogenoalkyl, C₁ -C₄ -halogenoalkoxy, or represents phenyl,phenoxy, phenylthio, phenyl-C₁ -C₄ -alkoxy or phenyl-C₁ -C₄ -alkylthio,each of which is optionally substituted by halogen, C₁ -C₆ -alkyl, C₁-C₆ -alkoxy, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -halogenoalkoxy, nitro orcyano.

X preferably represents hydrogen, halogen, C₁ -C₆ -alkyl, C₂ -C₆-alkenyl, C₂ -C₆ -alkinyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₄-halogenoalkyl, C₁ -C₄ -halogenoalkoxy, cyano, nitro, or representsphenyl, phenoxy, phenylthio, phenyl-C₁ -C₄ -alkoxy or phenyl-C₁ -C₄-alkylthio, each of which is optionally substituted by halogen, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C ₁ -C₄ -halogenoalkyl, C₁ -C₄ -halogenoalkoxy,nitro or cyano.

Y preferably represents hydrogen, halogen, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy, C₁ -C₆ -alkylthio, C₁ -C₄ -halogenoalkyl, C₁ -C₄-halogenoalkoxy, cyano or nitro.

Z preferably represents halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆-alkylthio, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -halogenoalkoxy, hydroxyl,cyano, nitro, or represents phenoxy, phenylthio, thiazolyloxy,pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-C₁ -C₄ -alkoxy orphenyl-C₁ -C₄ -alkylthio, each of which is optionally substituted byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkyl, C₁ -C₄-halogenoalkoxy, nitro or cyano, or

Y and Z preferably together represent C₃ -C₄ -alkanediyl, C₃ -C₄-alkenediyl or C₄ -alkanedienediyl which are in each case optionallysubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy or C₁ -C₄-halogenoalkyl and in which one to three members independently of oneanother can optionally be replaced by oxygen, sulphur, nitrogen or acarbonyl group, in which case n represents 1, or

W and Z preferably together represent C₃ -C₄ -alkanediyl, C,,-C₄-alkenediyl or C₄ -alkanedienediyl which are in each case optionallysubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy or C₁ -C₄-halogenoalkyl and in which one to three members independently of oneanother can optionally be replaced by oxygen, sulphur, nitrogen or acarbonyl group, in which case n represents 1, or

n preferably represents 0, 1 or 2, it being possible for thesubstituents Z to be identical or different if n=2.

Het preferably represents one of the groups ##STR32##

A preferably represents hydrogen, or represents C₁ -C₁₂ -alkyl, C₂ -C₈-alkenyl, C₁ -C₁₀ -alkoxy-C₁ -C₈ -alkyl, poly-C₁ -C₈ -alkoxy-C₁ -C₈-alkyl or C₁ -C₁₀ -alkylthio-C₁ -C₆ -alkyl, each of which is optionallysubstituted by halogen, or represents C₃ -C₈ -cycloalkyl which isoptionally substituted by halogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy andin which one or two methylene groups which are not directly adjacent areoptionally replaced by oxygen and/or sulphur, or represents phenyl,naphthyl, phenyl-C₁ -C₆ -alkyl, naphthyl-C₁ -C₆ -alkyl or hetaryl having5 or 6 ring atoms and one to three hetero atoms from the seriesconsisting of oxygen, sulphur and nitrogen, each of which is optionallysubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -halogenoalkyl, C₁ -C₆-alkoxy, C₁ -C₆ -halogenoalkoxy, cyano or nitro.

B preferably represents hydrogen, C₁ -C₁₂ -alkyl or C₁ -C₈ -alkoxy-C₁-C₆ -alkyl, or

A, B and the carbon atom to which they are bonded preferably representC₃ -C₁₀ -cycloalkyl or C₅ -C₁₀ -cycloalkenyl, in each of which onemethylene group is optionally replaced by oxygen or sulphur and whichare optionally substituted by C₁ -C₈ -alkyl, C₃ -C₁₀ -cycloalkyl, C₁ -C₈-halogenoalkyl, C₁ -C₈ -alkoxy, C₁ -C₈ -alkylthio, halogen or phenyl, or

A, B and the carbon atom to which they are bonded preferably representC₅ -C₆ -cycloalkyl which is substituted by an alkylenediyl group whichoptionally contains one or two oxygen and/or sulphur atoms or by analkylenedioxy group or by an alkylenedithioyl group, this group togetherwith the carbon atom to which it is bonded forming a further five- toeight-membered ring, or

A, B and the carbon atom to which they are bonded preferably representC₃ -C₈ -cycloalkyl or C₅ -C₈ -cycloalkenyl, in which two carbon atomsare connected by C₃ -C₆ -alkanediyl, C₃ -C₆ -alkenediyl or C₄ -C₆-alkanedienediyl, each of which is optionally substituted by C₁ -C₆-alkyl, C₁ -C₆ -alkoxy or halogen and in each of which one methylenegroup is optionally replaced by oxygen or sulphur.

D preferably represents hydrogen, or represents C₁ -C₁₂ -alkyl, C₃ -C₈-alkenyl, C₃ -C₈ -alkinyl, C₁ -C₁₀ -alkoxy-C₂ -C₈ -alkyl, poly-C₁ -C₈-alkoxy-C₂ -C₈ -alkyl or C₁ -C₁₀ -alkylthio-C₂ -C₈ -alkyl, each of whichis optionally substituted by halogen, or represents C₃ -C₈ -cycloalkylwhich is optionally substituted by halogen, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy or C₁ -C₄ -halogenoalkyl and in each of which one or twomethylene groups which are not directly adjacent are replaced by oxygenand/or sulphur, or represents phenyl, hetaryl having 5 or 6 ring atomsand one or two hetero atoms from the series consisting of oxygen,sulphur and nitrogen, phenyl-C₁ -C₆ -alkyl or hetaryl-C₁ -C₆ -alkylhaving 5 or 6 ring atoms and one or two hetero atoms from the seriesconsisting of oxygen, sulphur and nitrogen, each of which is optionallysubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -halogenoalkyl, C₁ -C₆-alkoxy, C₁ -C₆ -halogenoalkoxy, cyano or nitro, or

A and D together preferably represent a C₃ -C₆ -alkanediyl, C₃ -C₆-alkenediyl or C₄ -C₆ -alkanedienediyl group in each of which onemethylene group is optionally replaced by oxygen or sulphur and each ofwhich is optionally substituted by halogen or by C₁ -C₁₀ -alkyl, C₁ -C₆-alkoxy, C₁ -C₆ -alkylthio, C₃ -C₇ -cycloalkyl, phenyl or benzyloxy,each of which is optionally substituted by halogen, or by a further C₃-C₆ -alkanediyl, C₃ -C₆ -alkenediyl or C₄ -C₆ -alkanedienediyl groupwhich forms a fused ring and in each of which one methylene group isoptionally replaced by oxygen or sulphur and which are optionallysubstituted by C₁ -C₆ -alkyl, or

A and D together represent a C₃ -C₆ -alkanediyl or C₃ -C₆ -alkenediylgroup, each of which optionally contains one of the following groups##STR33##

G preferably represents hydrogen (a) or one of the groups ##STR34## inwhich

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ preferably represents C₁ -C₂₀ -alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈-alkoxy-C₁ -C₈ -alkyl, C₁ -C₈ -alkylthio-C₁ -C₈ -alkyl or poly-C₁ -C₈-alkoxy-C₁ -C₈ -alkyl, each of which is optionally substituted byhalogen, or represents C₃ -C₈ -cycloalkyl which is optionallysubstituted by halogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy and in which oneor two methylene groups which are not directly adjacent are optionallyreplaced by oxygen and/or sulphur, or represents phenyl which isoptionally substituted by halogen, cyano, nitro, C₁ -C₆ -alkyl, C₁ -C₆-alkoxy, C₁ -C₆ -halogenoalkyl, C₁ -C₆ -halogenoalkoxy, C₁ -C₆-alkylthio or C₁ -C₆ -alkylsulphonyl,

or represents phenyl-C₁ -C₆ -alkyl which is optionally substituted byhalogen, nitro, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆-halogenoalkyl or C₁ -C₆ -halogenoalkoxy,

or represents 5- or 6-membered hetaryl having one or two hetero atomsfrom the series consisting of oxygen, sulphur or nitrogen which isoptionally substituted by halogen or C₁ -C₆ -alkyl,

or represents phenoxy-C₁ -C₆ -alkyl which is optionally substituted byhalogen or C₁ -C₆ -alkyl,

or represents 5- or 6-membered hetaryloxy-C₁ -C₆ -alkyl having one ortwo hetero atoms from the series consisting of oxygen, sulphur andnitrogen which is optionally substituted by halogen, amino or C₁ -C₆-alkyl.

R² preferably represents C₁ -C₂₀ -alkyl, C₂ -C₂₀ -alkenyl, C₁ -C₈-alkoxy-C₂ -C₈ -alkyl or poly-C₁ -C₈ -alkoxy-C₂ -C₈ -alkyl, each ofwhich is optionally substituted by halogen,

or represents C₃ -C₈ -cycloalkyl which is optionally substituted byhalogen, C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy,

or represents phenyl or benzyl, each of which is optionally substitutedby halogen, cyano, nitro, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆-halogenoalkyl or C₁ -C₆ -halogenoalkoxy.

R³ preferably represents C₁ -C₈ -alkyl which is optionally substitutedby halogen, or represents phenyl or benzyl, each of which is optionallysubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₄-halogenoalkyl, C₁ -C₄ -halogenoalkoxy, cyano or nitro.

R⁴ and R⁵ independently of one another preferably represent C₁ -C₈-alkyl, C₁ -C₈ -alkoxy, C₁ -C₈ -alkylamino, di-(C₁ -C₈ -alkyl)amino, C₁-C₈ -alkylthio or C₃ -C₈ -alkenylthio each of which is optionallysubstituted by halogen, or represent phenyl, phenoxy or phenylthio, eachof which is optionally substituted by halogen, nitro, cyano, C₁ -C₄-alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-halogenoalkylthio, C₁ -C₄ -alkyl or C₁ -C₄ -halogenoalkyl.

R⁶ and R⁷ independently of one another preferably represent hydrogen, orrepresent C₁ -C₈ -alkyl, C₃ -C₈ -cycloalkyl, C₁ -C₈ -alkoxy, C₃ -C₈-alkenyl or C₁ -C₈ -alkoxy-C₂ -C₈ -alkyl, each of which is optionallysubstituted by halogen, or represent phenyl or benzyl, each of which isoptionally substituted by halogen, C₁ -C₈ -alkyl, C₁ -C₈ -halogenoalkylor C₁ -C₈ -alkoxy, or together represent a C₃ -C₆ -alkylene radical inwhich one methylene group is optionally replaced by oxygen or sulphurand which is optionally substituted by C₁ -C₆ -alkyl.

R¹³ preferably represents hydrogen, or represents C₁ -C₈ -alkyl or C₁-C₈ -alkoxy, each of which is optionally substituted by halogen, orrepresents C₃ -C₈ -cycloalkyl in which one methylene group is optionallyreplaced by oxygen or sulphur and which is optionally substituted byhalogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, or represents phenyl,phenyl-C₁ -C₄ -alkyl or phenyl-C₁ -C₄ -alkoxy, each of which isoptionally substituted by halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₄-halogenoalkyl, C₁ -C₄ -halogenoalkoxy, nitro or cyano.

R¹⁴ preferably represents hydrogen or C₁ -C₈ -alkyl, or

R¹³ and R¹⁴ together preferably represent C₄ -C₆ -alkanediyl.

R¹⁵ and R¹⁶ are identical or different and preferably represent C₁ -C₆-alkyl, or

R¹⁵ and R¹⁶ together preferably represent a C₂ -C₄ -alkanediyl radicalwhich is optionally substituted by C₁ -C₆ -alkyl or by phenyl which isoptionally substituted by halogen, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl,C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy, nitro or cyano.

R¹⁷ and R¹⁸ independently of one another preferably represent hydrogen,or represent C₁ -C₈ -alkyl which is optionally substituted by halogen,or represent phenyl which is optionally substituted by halogen, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -halogenoalkoxy,nitro or cyano, or

R¹⁷ and R¹⁸ together with the carbon atom to which they are bondedrepresent C₅ -C₇ -cycloalkyl in which one methylene group is optionallyreplaced by oxygen or sulphur and which is optionally substituted by C₁-C₄ -alkyl.

R¹⁹ and R²⁰ independently of one another preferably represent C₁ -C₁₀-alkyl, C₂ -C₁₀ -alkenyl, C₁ -C₁₀ -alkoxy, C₁ -C₁₀ -alkylamino, C₃ -C₁₀-alkenylamino, di-(C₁ -C₁₀ -alkyl)amino or di-(C₃ -C₁₀ -alkenyl)amino.

W especially preferably represents hydrogen, nitro, cyano, fluorine,chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁-C₂ -halogenoalkyl, C₁ -C₂ -halogenoalkoxy or represents phenyl,phenoxy, benzyl or benzyloxy, each of which is optionally substituted byfluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₂-halogenoalkyl, C₁ -C₂ -halogenoalkoxy, nitro or cyano.

X especially preferably represents hydrogen, fluorine, chlorine,bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₂-halogenoalkyl, C₁ -C₂ -halogenoalkoxy, cyano, nitro, or representsphenyl, phenoxy, benzyl or benzyloxy, each of which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, C₁ -C₂ -halogenoalkyl, C₁ -C₂ -halogenoalkoxy, nitro or cyano.

Y especially preferably represents hydrogen, fluorine, chlorine,bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₂-halogenoalkyl, C₁ -C₂ -halogenoalkoxy, cyano or nitro.

Z especially preferably represents fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₂ -halogenoalkyl, C₁ -C₂-halogenoalkoxy, hydroxyl, cyano, nitro, or represents phenoxy orbenzyloxy, each of which is optionally substituted by fluorine,chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₂ -halogenoalkyl,C₁ -C₂ -halogenoalkoxy, nitro or cyano.

n especially preferably represents 0 or 1.

Het especially preferably represents one of the groups ##STR35##

A especially preferably represents hydrogen, or represents C₁ -C₁₀-alkyl, C₂ -C₆ -alkenyl, C₁ -C₈ -alkoxy-C₁ -C₆ -alkyl, poly-C₁ -C₆-alkoxy-C₁ -C₆ -alkyl or C₁ -C₈ -alkylthio-C₁ -C₆ -alkyl, each of whichis optionally substituted by fluorine or chlorine, or represents C₃ -C₇-cycloalkyl in which one or two methylene groups which are not directlyadjacent are optionally replaced by oxygen and/or sulphur and which isoptionally substituted by fluorine, chlorine, C₁ -C₄ -alkyl or C₁ -C₄-alkoxy, or represents phenyl, furanyl, pyridyl, imidazolyl, triazolyl,pyrazolyl, indolyl, thiazolyl, thienyl or phenyl-C₁ -C₄ -alkyl, each ofwhich is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy,cyano or nitro.

B especially preferably represents hydrogen, C₁ -C₁₀ -alkyl or C₁ -C₆-alkoxy-C₁ -C₄ -alkyl, or

A, B and the carbon atom to which they are bonded especially preferablyrepresent C₃ -C₈ -cycloalkyl or C₅ -C₈ -cycloalkenyl, in each of whichone methylene group is optionally replaced by oxygen or sulphur andwhich are optionally substituted by C₁ -C₆ -alkyl or C₁ -C₆ -alkoxy, or

A, B and the carbon atom to which they are bonded especially preferablyrepresent C₅ -C₆ -cycloalkyl which is substituted by an alkylenediylgroup which optionally contains one or two oxygen or sulphur atoms or byan alkylenedioxy group or by an alkylenedithioyl group which, togetherwith the carbon atom to which it is bonded, forms a further five- toseven-membered ring, or

A, B and the carbon atom to which they are bonded especially preferablyrepresent C₃ -C₆ -cycloalkyl or C₁ -C₆ -cycloalkenyl in which two carbonatoms are connected by C₃ -C₅ -alkanediyl, C₃ -C₅ -alkenediyl orbutadienediyl, in each of which one methylene group is optionallyreplaced by oxygen or sulphur and which are optionally substituted by C₁-C₄ -alkyl or C₁ -C₄ -alkoxy.

D especially preferably represents hydrogen, or represents C₁ -C₁₀-alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₈ -alkoxy-C₂ -C₆ -alkyl,poly-C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl or C₁ -C₈ -alkylthio-C₂ -C₆ -alkyl,each of which is optionally substituted by fluorine or chlorine, orrepresents C₃ -C₇ -cycloalkyl, each of which is optionally substitutedby fluorine, chlorine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₂-halogenoalkyl and in which one or two methylene groups which are notdirectly adjacent are optionally replaced by oxygen and/or sulphur, orrepresents phenyl, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl,pyrimidyl, pyrrolyl, thienyl, triazolyl or phenyl-C₁ -C₄ -alkyl, each ofwhich is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄-alkyl, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy,cyano or nitro, or

A and D together especially preferably represent a C₃ -C₅ -alkanediyl orC₃ -C₅ -alkenediyl group, in each of which one methylene group isoptionally replaced by oxygen or sulphur and which are optionallysubstituted by fluorine, chlorine or by C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy,C₁ -C₄ -alkylthio, C₃ -C₆ -cycloalkyl, phenyl or benzyloxy, each ofwhich is optionally substituted by fluorine or chlorine, or

each of which optionally contains one of the following groups: ##STR36##

G especially preferably represents hydrogen (a) or one of the groups##STR37## in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ especially preferably represents C₁ -C₁₆ -alkyl, C₂ -C₁₆ -alkenyl, C₁-C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkylthio-C₁ -C₆ -alkyl or poly-C₁-C₆ -alkoxy-C₁ -C₆ -alkyl, each of which is optionally substituted byfluorine or chlorine, or represents C₃ -C₇ -cycloalkyl in which one ortwo methylene groups which are not directly adjacent are optionallyreplaced by oxygen and/or sulphur and which is optionally substituted byfluorine, chlorine, C₁ -C₅ -alkyl or C₁ -C₅ -alkoxy,

or represents phenyl which is optionally substituted by fluorine,chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃-halogenoalkyl, C₁ -C₃ -halogenoalkoxy, C₁ -C₄ -alkylthio or C₁ -C₄-alkylsulphonyl,

or represents phenyl-C₁ -C₄ -alkyl which is optionally substituted byfluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₃-halogenoalkyl or C₁ -C₃ -halogenoalkoxy,

or represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl orthienyl, each of which is optionally substituted by fluorine, chlorine,bromine or C₁ -C₄ -alkyl,

or represents phenoxy-C₁ -C₅ -alkyl which is optionally substituted byfluorine, chlorine, bromine or C₁ -C₄ -alkyl,

or represents pyridyloxy-C₁ -C₅ -alkyl, pyrimidyloxy-C₁ -C₅ -alkyl orthiazolyloxy-C₁ -C₅ -alkyl, each of which is optionally substituted byfluorine, chlorine, bromine, amino or C₁ -C₄ -alkyl.

R² especially preferably represents C₁ -C₁₆ -alkyl, C₂ -C₁₆ -alkenyl, C₁-C₆ -alkoxy-C₂ -C₆ -alkyl or poly-C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, each ofwhich is optionally substituted by fluorine or chlorine,

or represents C₃ -C₇ -cycloalkyl which is optionally substituted byfluorine, chlorine, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy,

or represents phenyl or benzyl, each of which is optionally substitutedby fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, C₁ -C₃-alkoxy, C₁ -C₃ -halogenoalkyl or C₁ -C₃ -halogenoalkoxy.

R³ especially preferably represents C₁ -C₆ -alkyl which is optionallysubstituted by fluorine or chlorine, or represents phenyl or benzyl,each of which is optionally substituted by fluorine, chlorine, bromine,C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₂ -halogenoalkoxy, C₁ -C₂-halogenoalkyl, cyano or nitro.

R⁴ and R⁵ independently of one another especially preferably representC₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylamino, di-(C₁ -C₆-alkyl)amino, C₁ -C₆ -alkylthio or C₃ -C₄ -alkenylthio, each of which isoptionally substituted by fluorine or chlorine, or represent phenyl,phenoxy or phenylthio, each of which is optionally substituted byfluorine, chlorine, bromine, nitro, cyano, C₁ -C₃ -alkoxy, C₁ -C₃-halogenoalkoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -halogenoalkylthio, C₁ -C₃-alkyl or C₁ -C₃ -halogenoalkyl.

R⁶ and R⁷ independently of one another especially preferably representhydrogen, or represent C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkoxy, C₃ -C₆ -alkenyl or C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, each of whichis optionally substituted by fluorine or chlorine, or represent phenylor benzyl, each of which is optionally substituted by fluorine,chlorine, bromine, C₁ -C₅ -halogenoalkyl, C₁ -C₅ -alkyl or C₁ -C₅-alkoxy, or together represent a C₃ -C₆ -alkylene radical which isoptionally substituted by C₁ -C₄ -alkyl and in which one methylene groupis optionally replaced by oxygen or sulphur.

R¹³ especially preferably represents hydrogen, or represents C₁ -C₆-alkyl or C₁ -C₆ -alkoxy, each of which is optionally substituted byfluorine or chlorine, or represents C₃ -C₇ -cycloalkyl in which onemethylene group is optionally replaced by oxygen or sulphur and which isoptionally substituted by fluorine, C₁ -C₂ -alkyl or C₁ -C₂ -alkoxy, orrepresents phenyl, phenyl-C₁ -C₃ -alkyl or phenyl-C₁ -C₂ -alkyloxy, eachof which is optionally substituted by fluorine, chlorine, bromine, C₁-C₅ -alkyl, C₁ -C₅ -alkoxy, C₁ -C₂ -halogenoalkyl, C₁ -C₂-halogenoalkoxy, nitro or cyano.

R¹⁴ especially preferably represents hydrogen or C₁ -C₆ -alkyl, or

R¹³ and R¹⁴ together especially preferably represent C₄ -C₆ -alkanediyl.

R¹⁵ and R¹⁶ are identical or different and represent especiallypreferably C₁ -C₄ -alkyl, or

R¹⁵ and R¹⁶ together especially preferably represent a C₂ -C₃-alkanediyl radical which is optionally substituted by C₁ -C₄ -alkyl orby phenyl which is optionally substituted by fluorine, chlorine,bromine, C₁ -C₂ -alkyl, C₁ -C₂ -halogenoalkyl, C₁ -C₂ -alkoxy, C₁ -C₂-halogenoalkoxy, nitro or cyano.

W very especially preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl.

X very especially preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl.

Y very especially preferably represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl.

Z very especially preferably represents fluorine, chlorine, bromine,methyl, ethyl, methoxy, ethoxy or trifluoromethyl.

n very especially preferably represents 0 or 1.

Het very especially preferably represents one of the groups ##STR38##

A very especially preferably represents hydrogen, or represents C₁ -C₈-alkyl, C₂ -C₄ -alkenyl, C₁ -C₆ -alkoxy-C₁ -C₄ -alkyl, poly-C₁ -C₄-alkoxy-C₁ -C₄ -alkyl or C₁ -C₆ -alkylthio-C₁ -C₄ -alkyl, each of whichis optionally substituted by fluorine or chlorine, or represents C₃ -C₆-cycloalkyl in which one or two methylene groups which are not directlyadjacent are optionally replaced by oxygen and/or sulphur and which isoptionally substituted by fluorine, chlorine, methyl or methoxy, orrepresents phenyl, pyridyl or benzyl, each of which is optionallysubstituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl,iso-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy.

B very especially preferably represents hydrogen, C₁ -C₈ -alkyl or C₁-C₄ -alkoxy-C₁ -C₂ -alkyl, or

A, B and the carbon atom to which they are bonded very especiallypreferably represent C₃ -C₈ -cycloalkyl or C₅ -C₈ -cycloalkenyl, in eachof which one methylene group is optionally replaced by oxygen or sulphurand which are optionally substituted by methyl, ethyl, n-propyl,iso-propyl, butyl, iso-butyl, sec-butyl, tert-butyl, methoxy, ethoxy,n-propoxy, iso-propoxy, butoxy, iso-butoxy, sec-butoxy or tert-butoxy,or

A, B and the carbon atom to which they are bonded very especiallypreferably represent C₁ -C₆ -cycloalkyl which is substituted by analkylenediyl group which optionally contains an oxygen or sulphur atomor by an alkylenedioxy group, this group together with the carbon atomto which it is bonded forming a further five- to six-membered ring, or

A, B and the carbon atom to which they are bonded very especiallypreferably represent C₃ -C₆ -cycloalkyl or C₅ -C₆ -cycloalkenyl in whichtwo carbon atoms are connected by C₃ -C₄ -alkanediyl, C₃ -C₄ -alkenediylor butadienediyl, in each of which one methylene group is optionallyreplaced by oxygen or sulphur.

D very especially preferably represents hydrogen, or represents C₁ -C₈-alkyl, C₃ -C₄ -alkenyl, C₃ -C₄ -alkinyl, C₁ -C₆ -alkoxy-C₂ -C₄ -alkyl,poly-C₁ -C₄ -alkoxy-C₂ -C₄ -alkyl, C₁ -C₄ -alkylthio-C₂ -C₄ -alkyl or C₃-C₆ -cycloalkyl in which one or two methylene groups which are notdirectly adjacent are optionally replaced by oxygen and/or sulphur andeach of which is optionally substituted by fluorine or chlorine, orrepresents phenyl, furanyl, pyridyl, thienyl or benzyl, each of which isoptionally substituted by fluorine, chlorine, bromine, methyl, ethyl,n-propyl, iso-propyl, methoxy, ethoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, or

A and D together very especially preferably represent a C₃ -C₅-alkanediyl or C₃ -C₅ -alkenediyl group, in each of which one methylenegroup is optionally replaced by oxygen or sulphur and which areoptionally substituted by fluorine, chlorine, methyl or methoxy.

G very especially preferably represents hydrogen (a) or one of thegroups ##STR39## in which

E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur.

R¹ very especially preferably represents C₁ -C₁₄ -alkyl, C₂ -C₁₄-alkenyl, C₁ -C₄ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₄ -alkylthio-C₁ -C₆ -alkyl,poly-C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, each of which is optionallysubstituted by fluorine or chlorine, or represents C₃ -C₆ -cycloalkyl inwhich one or two methylene groups which are not directly adjacent areoptionally replaced by oxygen and/or sulphur and which is optionallysubstituted by fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl,n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, n-propoxy or iso-propoxy,

or represents phenyl which is optionally substituted by fluorine,chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl,methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, methylthio,ethylthio, methylsulphonyl or ethylsulphonyl,

or represents benzyl which is optionally substituted by fluorine,chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, methoxy, ethoxy,trifluoromethyl or trifluoromethoxy,

or represents furanyl, thienyl or pyridyl, each of which is optionallysubstituted by fluorine, chlorine, bromine, methyl or ethyl,

or represents phenoxy-C₁ -C₄ -alkyl which is optionally substituted byfluorine, chlorine, methyl or ethyl,

or represents pyridyloxy-C₁ -C₄ -alkyl, pyrimidyloxy-C₁ -C₄ -alkyl orthiazolyloxy-C₁ -C₄ -alkyl, each of which is optionally substituted byfluorine, chlorine, amino, methyl or ethyl.

R² very especially preferably represents C₁ -C₁₄ -alkyl, C₂ -C₁₄-alkenyl, C₁ -C₄ -alkoxy-C₂ -C₆ -alkyl or poly-C₁ -C₄ -alkoxy-C₂ -C₆-alkyl, each of which is optionally substituted by fluorine or chlorine,

or represents C₃ -C₆ -cycloalkyl which is optionally substituted byfluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl or methoxy,

or is phenyl or benzyl, each of which is optionally substituted byfluorine, chlorine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl,methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,

R³ very especially preferably represents methyl, ethyl, propyl,iso-propyl, n-butyl, tert-butyl, each of which is optionally substitutedby fluorine or chlorine, or represents phenyl or benzyl, each of whichis optionally substituted by fluorine, chlorine, bromine, methyl, ethyl,iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro.

R⁴ and R⁵ independently of one another very especially preferablyrepresent C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylamino, di-(C₁ -C₄-alkyl)amino or C₁ -C₄ -alkylthio, each of which is optionallysubstituted by fluorine or chlorine, or represent phenyl, phenoxy orphenylthio, each of which is optionally substituted by fluorine,chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl ortrifluoromethoxy.

R⁶ and R⁷ independently of one another very especially preferablyrepresent hydrogen, or represent C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁-C₄ -alkoxy, C₃ -C₄ -alkenyl or C₁ -C₄ -alkoxy-C₂ -C₄ -alkyl, each ofwhich is optionally substituted by fluorine or chlorine, or representphenyl or benzyl, each of which is optionally substituted by fluorine,chlorine, bromine, methyl, methoxy or trifluoromethyl, or togetherrepresent a C₅ -C₆ -alkylene radical in which one methylene group isoptionally replaced by oxygen or sulphur and which is optionallysubstituted by methyl or ethyl.

The rule applies that W and Z together with the carbon atoms to whichthey are bonded may only then form a ring when these carbon atoms aredirectly adjacent.

The definitions of radicals or illustrations which have been mentionedabove in general or in preferred ranges can be combined with each otheras desired, that is to say combinations between the respective rangesand preferred ranges are also possible. They apply to the end productsand analogously to the precursors and intermediates.

Preferred according to the invention are those compounds of the formula(I) in which there is a combination of the meanings mentioned above asbeing preferred (preferable).

Especially preferred according to the invention are those compounds ofthe formula (I) in which there is a combination of the meaningsmentioned above as being especially preferred.

Very especially preferred according to the invention are those compoundsof the formula (I) in which there is a combination of the meaningsmentioned above as being very especially preferred.

An especially preferred group of compounds of the formula (I) is formedby those in which V¹ is nitrogen.

A further especially preferred group of compounds of the formula (I) isformed by those in which V² is nitrogen.

A further especially preferred group of compounds of the formula (I) isformed by those in which V³ is nitrogen.

Moreover, especially preferred compounds of the formula (I) are those inwhich G is hydrogen (a) or one of the groups ##STR40##

Moreover, especially preferred compounds of the formula (I) are those inwhich Het represents the group ##STR41##

Moreover, especially preferred compounds of the formula (I) are those inwhich Het represents the group ##STR42##

Moreover, especially preferred compounds of the formula (I) are those inwhich Het represents the group ##STR43##

As far as this is possible, saturated or unsaturated hydrocarbonradicals, such as alkyl or alkenyl, can be in each case straight-chainor branched, also in conjunction with hetero atoms such as, for example,in alkoxy.

Optionally substituted radicals can be monosubstituted orpolysubstituted, it being possible for the substituents to be identicalor different in the case of polysubstitutions.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be mentionedindividually: ##STR44##

                  TABLE 1                                                         ______________________________________                                        W = CH.sub.3 ; V.sup.1 = CCH.sub.3 ; V.sup.2 = N; V.sup.3 = CH; Z.sub.n =             A            B                                                        ______________________________________                                        CH.sub.3         H                                                              C.sub.2 H.sub.5 H                                                             C.sub.3 H.sub.7 H                                                             i-C.sub.3 H.sub.7 H                                                           C.sub.4 H.sub.9 H                                                             i-C.sub.4 H.sub.9 H                                                           s-C.sub.4 H.sub.9 H                                                           t-C.sub.4 H.sub.9 H                                                           CH.sub.3 CH.sub.3                                                             C.sub.2 H.sub.5 CH.sub.3                                                      C.sub.3 H.sub.7 CH.sub.3                                                      i-C.sub.3 H.sub.7 CH.sub.3                                                    C.sub.4 H.sub.9 CH.sub.3                                                      i-C.sub.4 H.sub.9 CH.sub.3                                                    s-C.sub.4 H.sub.9 CH.sub.3                                                    t-C.sub.4 H.sub.9 CH.sub.3                                                    C.sub.2 H.sub.5 C.sub.2 H.sub.5                                               C.sub.3 H.sub.7 C.sub.3 H.sub.7                                                -                                                                                             CH.sub.3                                                      -                                                                                             CH.sub.3                                                      -                                                                                             CH.sub.3                                                      -                                                                          --(CH.sub.2).sub.2 --                                                           --(CH.sub.2).sub.4 --                                                         --(CH.sub.2).sub.5 --                                                         --(CH.sub.2).sub.6 --                                                         --(CH.sub.2).sub.7 --                                                         --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --                                   --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.2 --                                   --CH.sub.2 --CHCH.sub.3 --(CH.sub.2).sub.3 --                                 --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.2 --                         --(CH.sub.2).sub.2 --CHC.sub.2 H.sub.5 --(CH.sub.2).sub.2 --                  --(CH.sub.2).sub.2 --CHC.sub.3 H.sub.7 --(CH.sub.2).sub.2 --                  --(CH.sub.2).sub.2 --CHi--C.sub.3 H.sub.7 --(CH.sub.2).sub.2 --              --(CH.sub.2).sub.2 --CHOCH.sub.3 --(CH.sub.2).sub.2 --                        --(CH.sub.2).sub.2 --CHOC.sub.2 H.sub.5 --(CH.sub.2).sub.2 --                 --(CH.sub.2).sub.2 --CHOC.sub.3 H.sub.7 --(CH.sub.2).sub.2 --                 --(CH.sub.2).sub.2 --CHOi--C.sub.3 H.sub.7 --(#.sub.2).sub.2 --               --(CH.sub.2).sub.2 --C(CH.sub.3).sub.2 --(CH.sub.2).sub.2 --                  --CH.sub.2 --(CHCH.sub.3).sub.2 --(CH.sub.2).sub.2 --                          -                                                                             #STR47##                                                                      -                                                                             #STR48##                                                                      -                                                                             #STR49##                                                                      -                                                                             #STR50##                                                                      -                                                                            ##STR51##                                                                    ______________________________________                                    

Table 2: A and B have the same meanings as in Table 1 and W═CH₃ ; V¹═CCl; V² ═N; V³ ═CH; Z_(n) ═H

Table 3: A and B have the same meanings as in Table 1 and W═CH₃ ; V¹═CCH₃ ; V² ═N; V³ ═CCH₃ ; Z_(n) ═H

Table 4: A and B have the same meanings as in Table 1 and W═H; V¹ ═CCl;V² ═N; V³ ═CH; Z_(n) ═H

Table 5: A and B have the same meanings as in Table 1 and W═CH₃ ; V¹ ═N;V² ═CH; V³ ═CCH₃ ; Z_(n) ═H

Table 6: A and B have the same meanings as in Table 1 and W=Cl; V¹ ═N;V² ═CH; V³ ═CCl; Z_(n) ═H

Table 7: A and B have the same meanings as in Table 1 and W═Cl; V¹ ═N;V² ═CH; V³ ═CCH₃ ; Z_(n) H

Table 8: A and B have the same meanings as in Table 1 and W═CH₃ ; V¹ ═N;V² ═CH; V³ ═CCl; Z_(n) H

Table 9: A and B have the same meanings as in Table 1 and W═CH₃ ; V¹═CH; V² ═CH; V³ ═N; Z_(n) ═H

Table 10: A and B have the same meanings as in Table 1 and W═H; V¹═C--Cl; V² ═N; V³ ═C--Cl; Z_(n) ═H

Table 11: A and B have the same meanings as in Table 1 and W═Cl; V¹ ═CH;V² ═N; V³ ═C--Cl; Z_(n) ═H

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-2-a) may be mentionedindividually:

                  TABLE 12                                                        ______________________________________                                          #STR52##                                                                      - W = CH.sub.3 ; V.sup.1 = CCH.sub.3 ; V.sup.2 = N; V.sup.3 = CH;           Z.sub.n = H                                                                           A            B                                                        ______________________________________                                        CH.sub.3         H                                                              C.sub.2 H.sub.5 H                                                             C.sub.3 H.sub.7 H                                                             i-C.sub.3 H.sub.7 H                                                           C.sub.4 H.sub.9 H                                                             i-C.sub.4 H.sub.9 H                                                           s-C.sub.4 H.sub.9 H                                                           t-C.sub.4 H.sub.9 H                                                           CH.sub.3 CH.sub.3                                                             C.sub.2 H.sub.5 CH.sub.3                                                      C.sub.3 H.sub.7 CH.sub.3                                                      i-C.sub.3 H.sub.7 CH.sub.3                                                    C.sub.4 H.sub.9 CH.sub.3                                                      i-C.sub.4 H.sub.9 CH.sub.3                                                    s-C.sub.4 H.sub.9 CH.sub.3                                                    t-C.sub.4 H.sub.9 CH.sub.3                                                    C.sub.2 H.sub.5 C.sub.2 H.sub.5                                               C.sub.3 H.sub.7 C.sub.3 H.sub.7                                                -                                                                                             CH.sub.3                                                      -                                                                                             CH.sub.3                                                      -                                                                                             CH.sub.3                                                      -                                                                          --(CH.sub.2).sub.2 --                                                           --(CH.sub.2).sub.4 --                                                         --(CH.sub.2).sub.5 --                                                         --(CH.sub.2).sub.6 --                                                         --(CH.sub.2).sub.7 --                                                         --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --                                   --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.2 --                                   --CH.sub.2 --CHCH.sub.3 --(CH.sub.2).sub.3 --                                 --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.2 --                         --(CH.sub.2).sub.2 --CHC.sub.2 H.sub.5 --(CH.sub.2).sub.2 --                  --(CH.sub.2).sub.2 --CHC.sub.3 H.sub.7 --(CH.sub.2).sub.2 --                  --(CH.sub.2).sub.2 --CHi--C.sub.3 H.sub.7 --(CH.sub.2).sub.2 --              --(CH.sub.2).sub.2 --CHOCH.sub.3 --(CH.sub.2).sub.2 --                        --(CH.sub.2).sub.2 --CHOC.sub.2 H.sub.5 --(CH.sub.2).sub.2 --                 --(CH.sub.2).sub.2 --CHOC.sub.3 H.sub.7 --(CH.sub.2).sub.2 --                 --(CH.sub.2).sub.2 --CHOi--C.sub.3 H.sub.7 --(CH.sub.2).sub.2 --              --(CH.sub.2).sub.2 --C(CH.sub.3).sub.2 --(CH.sub.2).sub.2 --                  --CH.sub.2 --(CHCH.sub.3).sub.2 --(CH.sub.2).sub.2 --                         --CH.sub.2 --CH --(CH.sub.2).sub.2 --                                          -                                                                             #STR56##                                                                      -                                                                             #STR57##                                                                      -                                                                             #STR58##                                                                      -                                                                             #STR59##                                                                      -                                                                            ##STR60##                                                                    ______________________________________                                    

Table 13: A and B have the same meanings as in Table 12 and W═CH₃ ; V¹═CCl; V² ═N; V³ ═CH; Z_(n)═H

Table 14: A and B have the same meanings as in Table 12 and W═CH₃ ; V¹═CCH₃ ; V² ═N; V³ ═CCH₃ ; Z_(n) ═H

Table 15: A and B have the same meanings as in Table 12 and W═H; V¹═CCl; V² ═N; V³ ═CH; Z_(n) ═H

Table 16: A and B have the same meanings as in Table 12 and W═CH₃ ; V¹═N; V² ═CH; V³ ═CCH₃ ; Z_(n) ═H

Table 17: A and B have the same meanings as in Table 12 and W═Cl; V¹ ═N;V² ═CH; V³ ═CCl; Z_(n) ═H

Table 18: A and B have the same meanings as in Table 12 and W═Cl; V¹ ═N;V² ═CH; V³ ═CCH₃ ; Z_(n) ═H

Table 19: A and B have the same meanings as in Table 12 and W═CH₃ ; V¹═N; V² ═CH; V³ ═CCl; Z_(n) ═H

Table 20: A and B have the same meanings as in Table 12 and W═CH₃ ; V¹═CH; V² ═CH; V³ ═N; Z_(n) ═H

Table 21: A and B have the same meanings as in Table 12 and W═H; V¹═C--Cl; V² ═N; V³ ═C--Cl; Z_(n) ═H

Table 22: A and B have the same meanings as in Table 12 and W═Cl; V¹═CH; V² ═N; V³ ═C--Cl; Z_(n) ═H

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-3-a) may be mentionedindividually:

                  TABLE 23                                                        ______________________________________                                          #STR61##                                                                      - W = CH.sub.3 ; V.sup.1 = CCH.sub.3 ; V.sup.2 = N; V.sup.3 = CH;           Z.sub.n = H                                                                           A            B                                                        ______________________________________                                        CH.sub.3         H                                                              C.sub.2 H.sub.5 H                                                             C.sub.3 H.sub.7 H                                                             i-C.sub.3 H.sub.7 H                                                           C.sub.4 H.sub.9 H                                                             i-C.sub.4 H.sub.9 H                                                           s-C.sub.4 H.sub.9 H                                                           t-C.sub.4 H.sub.9 H                                                           CH.sub.3 CH.sub.3                                                             C.sub.2 H.sub.5 CH.sub.3                                                      C.sub.3 H.sub.7 CH.sub.3                                                      i-C.sub.3 H.sub.7 CH.sub.3                                                    C.sub.4 H.sub.9 CH.sub.3                                                      i-C.sub.4 H.sub.9 CH.sub.3                                                    s-C.sub.4 H.sub.9 CH.sub.3                                                    t-C.sub.4 H.sub.9 CH.sub.3                                                    C.sub.2 H.sub.5 C.sub.2 H.sub.5                                               C.sub.3 H.sub.7 C.sub.3 H.sub.7                                                -                                                                                             CH.sub.3                                                      -                                                                                             CH.sub.3                                                      -                                                                                             CH.sub.3                                                      -                                                                          --(CH.sub.2).sub.2 --                                                           --(CH.sub.2).sub.4 --                                                         --(CH.sub.2).sub.5 --                                                         --(CH.sub.2).sub.6 --                                                         --(CH.sub.2).sub.7 --                                                         --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --                                   --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.2 --                                   --CH.sub.2 --CHCH.sub.3 --(CH.sub.2).sub.3 --                                 --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.2 --                         --(CH.sub.2).sub.2 --CHC.sub.2 H.sub.5 --(CH.sub.2).sub.2 --                  --(CH.sub.2).sub.2 --CHC.sub.3 H.sub.7 --(CH.sub.2).sub.2 --                  --(CH.sub.2).sub.2 --CHi--C.sub.3 H.sub.7 --(CH.sub.2).sub.2 --              --(CH.sub.2).sub.2 --CHOCH.sub.3 --(CH.sub.2).sub.2 --                        --(CH.sub.2).sub.2 --CHOC.sub.2 H.sub.5 --(CH.sub.2).sub.2 --                 --(CH.sub.2).sub.2 --CHOC.sub.3 H.sub.7 --(CH.sub.2).sub.2 --                 --(CH.sub.2).sub.2 --CHOi--C.sub.3 H.sub.7 --(CH.sub.2).sub.2 --              --(CH.sub.2).sub.2 --C(CH.sub.3).sub.2 --(CH.sub.2).sub.2 --                  --CH.sub.2 --(CHCH.sub.3).sub.2 --(CH.sub.2).sub.2 --                          -                                                                             #STR65##                                                                      -                                                                             #STR66##                                                                      -                                                                             #STR67##                                                                      -                                                                             #STR68##                                                                      -                                                                            ##STR69##                                                                    ______________________________________                                    

Table 24: A and B have the same meanings as in Table 23 and W═CH₃ ; V¹═CCl; V² ═N; V³ CH; Z_(n) ═H

Table 25: A and B have the same meanings as in Table 23 and W═CH₃ ; V¹═CCH₃ ; V² ═N; V³ ═CH₃ ; Z_(n) ═H

Table 26: A and B have the same meanings as in Table 23 and W═Cl; V¹ ═N;V² ═CH; V³ ═CCl; Z_(n) ═H

Table 27: A and B have the same meanings as in Table 23 and W═CH₃ ; V¹═CH; V² ═CH; V³ ═N; Z_(n) ═H

Table 28: A and B have the same meanings as in Table 23 and W═H; V¹═C--Cl; V² N; V³ ═C--Cl; Z_(n) ═H

Table 29: A and B have the same meanings as in Table 23 and W═Cl; V¹═CH; V² ═N; V³ ═C--Cl; Z_(n) ═H

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-4-a) may be mentionedindividually:

                  TABLE 30                                                        ______________________________________                                          #STR70##                                                                      - W = CH.sub.3 ; V.sup.1 = CCH.sub.3 ; V.sup.2 = N; V.sup.3 = CH;           Z.sub.n = H                                                                         A          D                                                            ______________________________________                                        H            CH.sub.3                                                           H C(CH.sub.3).sub.3                                                           H C(CH.sub.3).sub.2 CH.sub.2 Cl                                               CH.sub.3 CH.sub.3                                                             CH.sub.3 CH.sub.2 CHCH.sub.3 CH.sub.2 CH.sub.3                                H CH═C(CH.sub.3).sub.2                                                     - CH.sub.3                                                                                #STR71##                                                          - CH.sub.3                                                                                #STR72##                                                          - CH.sub.3                                                                                #STR73##                                                          - CH.sub.3                                                                                #STR74##                                                          - CH.sub.3                                                                                #STR75##                                                          -                                                                                         CH.sub.3                                                          - H                                                                                       #STR77##                                                          - CH.sub.3                                                                                #STR78##                                                          - CH.sub.3                                                                                #STR79##                                                          - CH.sub.3                                                                                #STR80##                                                          - CH.sub.3                                                                                #STR81##                                                          - H                                                                                       #STR82##                                                          - CH.sub.3 C.sub.5 H.sub.9                                                   CH.sub.3 C.sub.3 H.sub.5                                                      H C.sub.3 H.sub.4 Cl                                                        (CH.sub.2).sub.3                                                                (CH.sub.2).sub.4                                                              C(CH.sub.3).sub.2 OC(CH.sub.3).sub.2                                        ______________________________________                                    

Table 31: A and D have the same meanings as in Table 30 and W═CH₃ ; V¹═CCl; V² ═N; V³ ═CH; Z_(n) ═H

Table 32: A and D have the same meanings as in Table 30 and W═CH₃ ; V¹═CCH₃ ; V² ═N; V³ ═CCH₃ ; Z_(n) ═H

Table 33: A and D have the same meanings as in Table 30 and W═Cl; V¹ ═N;V² ═CH; V³ ═CCl; Z_(n) ═H

Table 34: A and D have the same meanings as in Table 30 and W═CH₃ ; V¹═CH; V² ═CH; V³ ═N; Z_(n) ═H

In addition to the compounds mentioned in the preparation examples, thefollowing compounds of the formula (I-5-a) may be mentionedindividually:

                  TABLE 35                                                        ______________________________________                                          #STR83##                                                                       - W = CH.sub.3 ; V.sup.1 = CCH.sub.3 ; V.sup.2 = N; V.sup.3 = CH;          Z.sub.n = H                                                                     A                                                                           ______________________________________                                        CH.sub.3                                                                        CH(CH.sub.3).sub.2                                                             -                                                                            #STR84##                                                                       -                                                                            #STR85##                                                                       -                                                                            #STR86##                                                                       -                                                                           ##STR87##                                                                    ______________________________________                                    

Table 36: A has the same meaning as in Table 35 and W═CH₃ ; V¹ ═CCl; V²═N; V³ ═CH; Z_(n) ═H

Table 37: A has the same meaning as in Table 35 and W═CH₃ ; V¹ ═CCH₃ ;V² ═N; V³ ═CCH₃ ; Z_(n) ═H

Table 38: A has the same meaning as in Table 35 and W═Cl; V¹ ═N; V² ═CH;V³ ═CCl; Z_(n) ═H

Table 39: A has the same meaning as in Table 35 and W═CH₃ ; V¹ ═CH; V²═CH; V³ ═N; Z_(n) ═H

If, in accordance with process (A), ethylN-[3-(6-chloro-2,4-dimethyl)-pyridylacetyl]-1-amino-4-ethyl-cyclohexane-carboxylateis used as starting substance, the course of the process according tothe invention can be represented by the following equation: ##STR88##

If, in accordance with process (B), ethylO-[4-(3-chloro-5-methyl)-pyridylacetyl]-hydroxyacetate is used, thecourse of the process according to the invention can be represented bythe following equation: ##STR89##

If, in accordance with process (C), ethyl2-[2-(3-chloro-5-methyl)-pyridyl]-4-(4-methoxy)-benzylmercapto-4-methyl-3-oxo-valerateis used as starting substance, the course of the process according tothe invention can be represented by the following equation: ##STR90##

For example, if, in accordance with process (D), chlorocarbonyl2-[3-(6-chloro-2,4-dimethyl)-pyridyl] ketene and acetone are used asstarting compounds, the course of the process according to the inventioncan be represented by the following equation: ##STR91##

For example, if, in accordance with process (E), chlorocarbonyl2-[3-(2,4,6-trimethyl)-pyridyl] ketene and thiobenzamide are used asstarting compounds, the course of the process according to the inventioncan be represented by the following equation: ##STR92##

If, in accordance with process (Fα),3-[4-(3-chloro-5-methyl)-pyridyl]-5,5-dimethyl-pyrrolidine-2,4-dione andpivaloyl chloride are used as starting materials, the course of theprocess according to the invention can be represented by the followingequation: ##STR93##

If, in accordance with process (F) (variant β),3-[2-(3-chloro)-pyridyl]-4-hydroxy-5-phenyl-Δ³ -dihydrofuran-2-one andacetic anhydride are used as starting compounds, the course of theprocess according to the invention can be represented by the followingequation: ##STR94##

If, in accordance with process (G),8-[2-(3,5-dichloro-4-methyl)-pyridyl]-5,5-pentamethylene-pyrrolidine-2,4-dioneand ethoxyethyl chloroformate are used as starting compounds, the courseof the process according to the invention can be represented by thefollowing equation: ##STR95##

If, in accordance with process (H) (variant α),3-[2-(3-bromo-5,6-dimethyl)-pyridyl]-4-hydroxy-6-(3-pyridyl)-pyrone andmethyl chloromonothioformate are used as starting materials, the courseof the process according to the invention can be represented as follows:##STR96##

If, in accordance with process (H) (variant β),5-[4-(2-chloro-3,5-dimethyl)-pyridyl]-6-hydroxy-2-(4-chlorophenyl)-thiazin-4-one,carbon disulphide and methyl iodide are used as starting components, thecourse of the reaction can be represented as follows: ##STR97##

If, in accordance with process (I),2-[3-(2,4,6-trimethyl)-pyridyl]-5,5[-3-methyl)pentamethylene-pyrrolidine-2,4-dioneand methanesulphonyl chloride are used as starting materials, the courseof the reaction can be represented by the following equation: ##STR98##

If, in accordance with process (J),2-[4-(3-chloro-5-methyl)-pyridyl]-4-hydroxy-5-methyl-6-(2-pyridyl)-pyroneand 2,2,2-trifluoroethyl methanechlorothiophosphonate are used asstarting materials, the course of the reaction can be represented by thefollowing equation: ##STR99##

If, in accordance with process (K),3-[3-(2,6-dichloro)-4-methylpyridyl]-5-cyclopropyl-5-methyl-pyrrolidine-2,4-dioneand NaOH are used as components, the course of the process according tothe invention can be represented by the following equation: ##STR100##

If, in accordance with process (L) (variant α),3-[3-(2-chloro-6-bromo-5-methyl)-pyridyl]-4-hydroxy-5,5-tetramethylene-.DELTA.³-dihydro-furan-2-one and ethyl isocyanate are used as startingmaterials, the course of the reaction can be represented by thefollowing equation: ##STR101##

If, in accordance with process (L) (variant β),3-[4-(3-chloro-5-methyl)-pyridyl]-5-methyl-pyrrolidine-2,4-dione anddimethylcarbamoyl chloride are used as starting materials, the course ofthe reaction can be represented by the following equation: ##STR102##

The compounds of the formula (II) ##STR103## in which

A, B, W, X, Z, V¹, V², V³, n and R⁸ have the abovementioned meanings andwhich are required as starting materials in process (A) according to theinvention are new.

For example, the acylamino acid esters of the formula (II) are obtainedwhen amino acid derivatives of the formula (XIX) ##STR104## in which

A, B and R⁸ have the abovementioned meanings are acylated withsubstituted pyridylacetic acid halides of the formula (XX) ##STR105## inwhich

W, V¹, V², V³, n and Z have the abovementioned meanings and Halrepresents chlorine or bromine, (Chem. Reviews 52, 237-416 (1953);Bhattacharya, Indian J. Chem. 6 341-5, 1968), or when acylamino acids ofthe formula (XXI) ##STR106## in which

A, B, W, V¹, V², V³, n and Z have the abovementioned meanings areesterified (Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XXI) ##STR107## in which

A, B, W, V¹, V², V³, n and Z have the abovementioned meanings are new.

The compounds of the formula (XXI) are obtained when amino acids of theformula (XXII) ##STR108## in which

A and B have the abovementioned meanings are acylated with substitutedpyridylacetic acid halides of the formula (XX) ##STR109## in which

W, V¹, V², V³, n and Z have the abovementioned meanings and Halrepresents chlorine or bromine by the method of Schotten-Baumann(Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p.505).

Some of the compounds of the formula (XX) are new. They can be preparedby known processes.

For example, the compounds of the formula (XX) are obtained by reactingsubstituted pyridylacetic acids of the formula (XXIII) ##STR110## inwhich

W, V¹, V², V³, n and Z have the abovementioned meanings withhalogenating agents (for example thionyl chloride, thionyl bromide,oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromideor phosphorus pentachloride) at temperatures from -20° C. to 150° C.,preferably from -10° C. to 100° C., if appropriate in the presence of adiluent (for example optionally chlorinated aliphatic or aromatichydrocarbons such as toluene or methylene chloride).

Some of the compounds of the formula (XXIII) are new. They can beprepared by processes known from the literature (see, for example,Organikum, 15th Edition, p. 533, VEB Deutscher Verlag derWissenschaften, Berlin 1977 and the Preparation Examples). The compoundsof the formula (XXIII) are obtained, for example, by hydrolysingsubstituted pyridylacetic acid esters of the formula (XXIV) ##STR111##in which

W, V¹, V², V³, n, Z and R⁸ have the abovementioned meanings attemperatures between 0° C. and 150° C., preferably between 20° C. and100° C., in the presence of an acid (for example an inorganic acid suchas hydrochloric acid) or of a base (for example an alkali metalhydroxide such as sodium hydroxide or potassium hydroxide) and, ifappropriate, of a diluent (for example an aqueous alcohol such asmethanol or ethanol).

Some of the compounds of the formula (XXIV) are new. They can beprepared by processes known in principle.

For example, the compounds of the formula (XXIV) are obtained byreacting substituted 1,1,1-trichloro-2-pyridylethanes of the formula(XXV) ##STR112## in which

W, V¹, V², V³, n and Z have the abovementioned meanings first withalkoxides (for example alkali metal alkoxides such as sodium methoxideor sodium ethoxide) in the presence of a diluent (for example thealcohol derived from the alkoxide) at temperatures between 0° C. and150° C., preferably between 20° C. and 120° C., and subsequently with anacid (preferably an inorganic acid such as, for example, sulphuric acid)at temperatures between -20° C. and 150° C., preferably 0° C. and 100°C. (cf DE 3 314 249).

The compounds of the formula (XXV) are new. They can be prepared byprocesses known in principle.

For example, the compounds of the formula (XXV) are obtained whenaminopyridines of the formula (XXVI) ##STR113## in which

W, V¹, V², V³, n and Z have the abovementioned meanings are reacted withvinylidene chloride (CH₂ ═CCl₂) in the presence of an alkyl nitrite ofthe formula (XXVII)

    R.sup.21 --ONO                                             (XXVII)

in which

R²¹ represents alkyl, preferably C₁ -C₆ -alkyl, in the presence ofcopper(II) chloride and, if appropriate, in the presence of a diluent(for example an aliphatic nitrile such as acetonitrile) at a temperatureof -20° C. to 80° C., preferably 0° C. to 60° C.

The compounds of the formulae (XXVI) and (XXVII) are known compounds oforganic chemistry. Copper(II) chloride and vinylidene chloride have beenknown for a long time and are commercially available.

The compounds of the formulae (XIX) and (XXII) are known in some casesand/or can be synthesized by known processes (see, for example,Compagnon, Ann. Chim. (Paris) [14] 5, pp. 11-22, 23-27 (1970)).

The substituted cyclic aminocarboxylic acids of the formula (XXIIa) inwhich A and B form a ring are generally obtainable by a Bucherer-Bergssynthesis or by a Strecker synthesis, where they are obtained in eachcase in different isomeric forms. Thus, the conditions of theBucherer-Bergs synthesis preferentially yields the isomers (termed 13hereinbelow for the sake of simplicity) in which the radicals R and thecarboxyl group are in the equatorial position, while the conditions ofthe Strecker synthesis preferentially yield the isomers (termed αhereinbelow for the sake of simplicity) in which the amino group and theradicals R are in the equatorial position ##STR114##

(L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, C. Jitrangeri, Can.J. Chem. 53, 3339 (1975)).

Moreover, the starting materials of the formula (II) ##STR115## in which

A, B, W, V¹, V², V³, n, Z and R⁸ have the abovementioned meanings andwhich are used in the above process (A) can be prepared whenaminonitriles of the formula (XXVIII) ##STR116## in which

A and B have the abovementioned meanings are reacted with substitutedpyridylacetic acid halides of the formula (XX) ##STR117## in which

W, V¹, V², V³, n, Z and Hal have the abovementioned meanings to givecompounds of the formula (XXIX) ##STR118## in which

A, B, W, V¹, V², V³, n and Z have the abovementioned meanings and theseare subsequently subjected to acid alcoholysis.

The compounds of the formula (XXIX) are also new.

The compounds of the formula (III) ##STR119## in which

A, B, W, V¹, V², V³, n, Z and R⁸ have the abovementioned meanings andwhich are required as starting materials in process (B) according to theinvention are new.

They can be prepared in a simple manner by methods known in principle.

The compounds of the formula (III) are obtained, for example when2-hydroxycarboxylic esters of the formula (XXX) ##STR120## in which

A, B and R⁸ have the abovementioned meanings are acylated withsubstituted pyridylacetyl halides of the formula (XX) ##STR121## inwhich

W, V¹, V², V³, n, Z and Hal have the abovementioned meanings (Chem.Reviews 52, 237-416 (1953)).

Moreover, compounds of the formula (III) are obtained when substitutedpyridylacetic acids of the formula (XXIII) ##STR122## in which

W, V¹, V², V³, n and Z have the abovementioned meanings are alkylatedwith a-halogenocarboxylic esters of the formula (XXXI) ##STR123## inwhich

A, B and R⁸ have the abovementioned meanings and Hal represents chlorineor bromine.

The compounds of the formula (XXXI) are commercially available or can beprepared in a simple manner by known methods.

The compounds of the formula (IV) ##STR124## in which

A, B, T, W, V¹, V², V³, n, Z and R⁸ have the abovementioned meanings andwhich are required as starting materials in the above process (C) arenew.

They can be prepared by methods known in principle.

The compounds of the formula (IV) are obtained, for example, whensubstituted pyridylacetic esters of the formula (XXIV) ##STR125## inwhich

W, V¹, V², V³, n, R⁸ and Z have the abovementioned meanings are acylatedwith 2-benzylthio-carboxylic acid halides of the formula (XXXII)##STR126## in which

A, B and T have the abovementioned meanings and Hal represents halogen(in particular chlorine or bromine) in the presence of strong bases(see, for example, M. S. Chambers, E. J. Thomas, D. J. Williams, J.Chem. Soc. Chem. Commun., (1987), 1228).

The benzylthio-carboxylic acid halides of the formula (XXXII) are knownin some cases and/or can be prepared by known methods (J. Antibiotics(1983), 26, 1589).

The halogenocarbonyl ketenes of the formula (VI) which are required asstarting materials in process (D) are new. They can be prepared in asimple manner by methods known in principle (cf., for example, Org.Prep. Proced. Int. 7, (4), 155-158, 1975 and DE 1 945 703). Thecompounds of the formula (VI) ##STR127## in which

W, V¹, V², V³, n and Z have the abovementioned meanings and Halrepresents chlorine or bromine are obtained when substitutedpyridylmalonic acids of the formula (XXXIII) ##STR128## in which

W, V¹, V², V³, n and Z have the abovementioned meanings are reacted withacid halides such as, for example, thionyl chloride, phosphorus(V)chloride, phosphorus(III) chloride, oxalyl chloride, phosgene or thionylbromide, if appropriate in the presence of catalysts such as, forexample, diethylformamide, methyl-sterylformamide or triphenylphosphineand, if appropriate, in the presence of bases such as, for example,pyridine or triethylamine at a temperature between -20° C. and 200° C.,preferably between 0° C. and 150° C.

The substituted pyridylmalonic acids of the formula (XXXIII) are new.However. they can be prepared in a simple manner by known processes(cf., for example, Organikum, VEB Deutscher Verlag der Wissenschaften,Berlin 1977, p. 517 et seq.), for example by hydrolysing substitutedpyridylmalonic esters of the formula (XXXIV) ##STR129## in which

W, V¹, V², V³, n, Z and R⁸ have the abovementioned meanings.

The carbonyl compounds of the formula (V) or their silyl enol ethers ofthe formula (Va) ##STR130## in which

A, D and R⁸ have the abovementioned meanings and which are required asstarting materials for process (E) according to the invention arecompounds which are commercially available, generally known oraccessible by known methods.

The preparation of the ketene acid chlorides of the formula (VI) whichare required as starting materials for carrying out process (E)according to the invention has already been described in process (D)according to the invention. The thioamides of the formula (VII)##STR131## in which

A has the abovementioned meaning and which are required for carrying outprocess (E) according to the invention are compounds generally known inorganic chemistry.

The malonic esters of the formula (XXXIV) ##STR132## in which R⁸, W, V¹,V², V³, n and Z have the abovementioned meanings are new. They can besynthesized by generally known methods of organic chemistry (cf., forexample, Tetrahedron Lett. 27, 2763 (1986) and Organikum, VEB DeutscherVerlag der Wissenschaften, Berlin 1977, p. 587 et seq.).

The acid halides of the formula (VIII), carboxylic anhydrides of theformula (IX), chloroformic esters or chloroformic thioesters of theformula (X), chloromonothioformic esters or chlorodithioformic esters ofthe formula (XI), alkyl halides of the formula (XII), sulphonylchlorides of the formula (XIII), phosphorus compounds of the formula(XIV) and metal hydroxides, metal alkoxides or amines of the formula(XV) and (XVI) and isocyanates of the formula (XVII) and carbamoylchlorides of the formula (XVIII), all of which are furthermore requiredas starting materials for carrying out processes (F), (G), (H), (I),(J), (K) and (L) according to the invention, are generally knowncompounds of organic or inorganic chemistry.

In addition, the compounds of the formulae (V), (Va), (VII) to (XIX),(XXII), (XXVIII), (XXX), (XXXI) and (XXXII) are disclosed in the patentapplications cited at the outset and/or can be prepared by the methodsgiven therein.

Process (A) is characterized in that compounds of the formula (II) inwhich A, B, W, V¹, V², V³, n, Z and R⁸ have the abovementioned meaningsare subjected to an intramolecular condensation reaction in the presenceof a diluent and in the presence of a base.

Diluents which may be employed in process (A) according to the inventionare all organic solvents which are inert to the reactants. The followingmay preferably be used: hydrocarbons such as toluene and xylene,furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone, and alcohols such as methanol, ethanol, propanol,iso-propanol, butanol, iso-butanol and tert-butanol.

Bases (deprotonating agents) which can be employed when carrying outprocess (A) according to the invention are all customary protonacceptors. The following may preferably be used: alkali metal oxides,alkali metal hydroxides, alkali metal carbonates, alkaline earth metaloxides, alkaline earth metal hydroxides and alkaline earth metalcarbonates such as sodium hydroxide, potassium hydroxide, magnesiumoxide, calcium oxide, sodium carbonate, potassium carbonate and calciumcarbonate, all of which can also be employed in the presence of phasetransfer catalysts such as, for example, triethylbenzylammoniumchloride, tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1 (=tris-(methoxyethyoxyethyl)-amine).Moreover, alkali metals such as sodium or potassium can be used.Substances which may also be employed are alkali metal amides, alkalimetal hydrides, alkaline earth metal amides and alkaline earth metalhydrides such as sodium amide, sodium hydride and calcium hydride, andfurthermore also alkali metal alkoxides, such as sodium methoxide,sodium ethoxide and potassium tert-butoxide.

When carrying out process (A) according to the invention, the reactiontemperature can be varied within a substantial range. In general, theprocess is carried out at temperatures between -70° C. and 150° C.,preferably between -50° C. and 100° C.

Process (A) according to the invention is generally carried out underatmospheric, pressure.

When carrying out process (A) according to the invention, the reactantof the formula (II) and the deprotonating base are generally employed inequimolar to approximately twice the equimolar amounts. However, it isalso possible to use one or the other component in a larger excess (upto 3 mol).

Process (B) is characterized in that compounds of the formula (III) inwhich A, B, W, V¹, V², V³, n, Z and R⁸ have the abovementioned meaningsare subjected to an intramolecular condensation reaction in the presenceof a diluent and in the presence of a base.

Diluents which may be employed in process (B) according to the inventionare all organic solvents which are inert to the reactants. The followingmay preferably be used: hydrocarbons such as toluene and xylene,furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, moreover polarsolvents such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone. Moreover, alcohols such as methanol, ethanol,propanol, iso-propanol, butanol, iso-butanol and tert-butanol can beemployed.

Bases (deprotonating agents) which can be employed when carrying outprocess (B) according to the invention are all customary protonacceptors. The following may preferably be used: alkali metal oxides,alkali metal hydroxides, alkali metal carbonates, alkaline earth metaloxides, alkaline earth metal hydroxides and alkaline earth metalcarbonates such as sodium hydroxide, potassium hydroxide, magnesiumoxide, calcium oxide, sodium carbonate, potassium carbonate and calciumcarbonate, all of which can also be employed in the presence of phasetransfer catalysts such as, for example, triethylbenzylammoniumchloride, tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1 (=tris-(methoxyethyoxyethyl)-amine).Moreover, alkali metals such as sodium or potassium can be used.Substances which may also be employed are alkali metal amides, alkalimetal hydrides, alkaline earth metal amides and alkaline earth metalhydrides such as sodium amide, sodium hydride and calcium hydride, andfurthermore also alkali metal alkoxides, such as sodium methoxide,sodium ethoxide and potassium tert-butoxide.

When carrying out process (B) according to the invention, the reactiontemperature can be varied within a substantial range. In general, theprocess is carried out at temperatures between -75° C. and 150° C.,preferably between -50° C. and 100° C.

Process (B) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (B) according to the invention, the reactantsof the formula (III) and the deprotonating bases are generally employedin approximately equimolar amounts. However, it is also possible to useone or the other component in a larger excess (up to 3 mol).

Process (C) is characterized in that compounds of the formula (IV) inwhich A, B, T, W, V¹, V², V³, n, Z and R⁸ have the abovementionedmeanings are subjected to an intramolecular cyclization reaction in thepresence of an acid and, if appropriate, in the presence of a diluent.

Diluents which can be employed in process (C) according to the inventionare all organic solvents which are inert to the reactants. The followingmay preferably be used: hydrocarbons such as toluene and xylene,furthermore halogenated hydrocarbons such as dichloromethane,chloroform, ethylene chloride, chlorobenzene, dichlorobenzene,furthermore polar solvents such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methyl-pyrrolidone. Moreover, alcohols such asmethanol, ethanol, propanol, iso-propanol, butanol, iso-butanol andtert-butanol can be employed.

If appropriate, the acid employed may also act as the diluent.

Acids which can be employed in process (C) according to the inventionare all customary inorganic and organic acids such as, for example,hydrohalic acids, sulphuric acid, alkyl-, aryl- and haloalkylsulphonicacids; in particular, halogenated alkylcarboxylic acids such as, forexample, trifluoroacetic acid, are used.

When carrying out process (C) according to the invention, the reactiontemperature can be varied within a substantial range. In general, theprocess is carried out at temperatures between 0° C. and 250° C.,preferably between 50° C. and 150° C.

Process (C) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (C) according to the invention, the reactantsof the formula (IV) and the acid are employed, for example, in equimolaramounts. However, if appropriate, it is also possible to employ the acidin catalytic amounts.

Process (D) according to the invention is characterized in that carbonylcompounds of the formula (V) or silyl enol ethers thereof of the formula(Va), in which formulae A and B have the abovementioned meanings, arereacted with ketene acid halides of the formula (VI) in which W, V¹, V²,V³, n and Z have the abovementioned meanings, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidacceptor.

Diluents which can be employed in process (D) according to the inventionare all organic solvents which are inert to the reactants. Thefollowing(may preferably be used: hydrocarbons such aso-dichlorobenzene, tetralin, toluene and xylene, furthermore ethers suchas dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, andfurthermore polar solvents such as dimethyl sulphoxide, sulpholane,dimethylformamide or N-methyl-pyrrolidone.

Acid acceptors which can be used when carrying out process (D) accordingto the invention are all customary acid acceptors.

The following may preferably be used: tertiary amines such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base orN,N-dimethyl-aniline.

When carrying out process (D) according to the invention, the reactiontemperature can be varied within a substantial range. Expediently, theprocess is carried out at temperatures between 0° C. and 250° C.,preferably between 50° C. and 220° C.

Process (D) according to the invention is preferably carried out underatmospheric pressure.

When carrying out process (D) according to the invention, the reactantsof the formulae (V) and (VI) and, if appropriate, the acid acceptor aregenerally employed in approximately equimolar amounts. However, it isalso possible to use one or the other component in a larger excess (upto 5 mol).

Process (E) according to the invention is characterized in thatthioamides of the formula (VII) in which A has the abovementionedmeaning, are reacted with ketene acid halides of the formula (VI) inwhich W, V¹, V², V³, n and Z have the abovementioned meanings, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid acceptor.

Diluents which can be employed in process variant (E) according to theinvention are all inert organic solvents. The following may preferablybe used: hydrocarbons such as o-dichlorobenzene, tetralin, toluene andxylene, furthermore ethers such as dibutyl ether, glycol dimethyl etherand diglycol dimethyl ether, and furthermore polar solvents such asdimethyl sulphoxide, sulpholane, dimethylformamide orN-methyl-pyrrolidone.

Acid acceptors which can be used when carrying out process (E) accordingto the invention are all customary acid acceptors.

The following may preferably be used: tertiary amines such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base orN,N-dimethyl-aniline.

When carrying out process (E) according to the invention, the reactiontemperature can be varied within a substantial range. Expediently, theprocess is carried out at temperatures between 0° C. and 250° C.,preferably between 20° C. and 220° C.

Process (E) according to the invention is preferably carried out underatmospheric pressure.

When carrying out process (E) according to the invention, the reactantsof the formulae (VII) and (VI) and, if appropriate, the acid acceptorsare generally employed in approximately equimolar amounts. However, itis also possible to use one or the other component in a larger excess(up to 5 mol).

Process (Fα) is characterized in that compounds of the formulae (I-1-a)to (I-5-a) are in each case reacted with carboxylic acid halides of theformula (VIII), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid-binding agent.

Diluents which can be employed in process (Fα) according to theinvention are all solvents which are inert to the acid halides. Thefollowing may preferably be used: hydrocarbons such as benzine, benzene,toluene, xylene and tetralin, furthermore halogenohydrocarbons such asmethylene chloride, chloroform, carbon tetra-chloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers such as diethyl ether,tetrahydrofuran and dioxane, in addition carboxylic esters, such asethyl acetate, and also strongly polar solvents such asdimethylformamide, dimethyl sulphoxide and sulpholane. If the acidhalide is sufficiently stable to hydrolysis, the reaction can also becarried out in the presence of water.

Acid binders which are suitable when carrying out the reaction inaccordance with process (Fα) according to the invention are allcustomary acid acceptors. The following may preferably be used: tertiaryamines such as triethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base andN,N-dimethyl-aniline, furthermore alkaline earth metal oxides such asmagnesium oxide and calcium oxide, moreover alkali metal carbonates andalkaline earth metal carbonates such as sodium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal hydroxides suchas sodium hydroxide and potassium hydroxide.

When carrying out process (Fα) according to the invention, the reactiontemperature can be varied within a substantial range. In general, theprocess is carried out at temperatures between -20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out process (Fα) according to the invention, the startingmaterials of the formulae (I-1-a) to (I-5-a) and the carboxylic acidhalide of the formula (VIII) are generally in each case used inapproximately equivalent amounts. However, it is also possible to employthe carboxylic acid halide in a larger excess (up to 5 mol). Working-upis carried out by customary methods.

Process (Fβ) is characterized in that compounds of the formulae (I-1-a)to (I-5-a) are in each case reacted with carboxylic anhydrides of theformula (IX), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid-binding agent.

Diluents which can be employed in process (Fβ) according to theinvention are preferably those diluents which are also suitable whenacid halides are used. Besides, a carboxylic anhydride employed in anexcess can also simultaneously act as the diluent.

Acid binders which are optionally added in process (Fβ) are preferablythose acid binders which are also suitable when acid halides are used.

When carrying out process (Fβ) according to the invention, the reactiontemperature can be varied within a substantial range. In general, theprocess is carried out at temperatures between -20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out process (Fβ) according to the invention, the startingmaterials of the formulae (I-1-a) to (I-5-a) and the carboxylicanhydride of the formula (IX) are generally in each case used inapproximately equivalent amounts. However, it is also possible to employthe carboxylic anhydride in a larger excess (up to 5 mol). Working-up iscarried out by customary methods.

In general, a procedure is followed in which diluent and excesscarboxylic anhydride and also the carboxylic acid being formed areremoved by distillation by washing with an organic solvent or withwater.

Process (G) is characterized in that compounds of the formulae (I-1-a)to (I-5-a) are reacted in each case with chloroformic esters orchloroformic thioesters of the formula (X), if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.

Acid binders which are suitable for process (G) according to theinvention are all customary acid acceptors. The following may preferablybe used: tertiary amines such as triethylamine, pyridine, DABCO, DBU,DBA, Hunig base and N,N-dimethyl-aniline, furthermore alkaline earthmetal oxides such as magnesium oxide and calcium oxide, moreover alkalimetal carbonates and alkaline earth metal carbonates such as sodiumcarbonate, potassium carbonate and calcium carbonate, and also alkalimetal hydroxides such as sodium hydroxide and potassium hydroxide.

Diluents which can be employed in process (G) according to the inventionare all solvents which are inert to the chloroformic esters orchloroformic thioesters. The following may preferably be used:hydrocarbons such as benzine, benzene, toluene, xylene and tetralin,furthermore halogenohydrocarbons such as methylene chloride, chloroform,carbon tetrachloride, chlorobenzene and o-dichlorobenzene, moreoverketones, such as acetone and methyl isopropyl ketone, furthermore etherssuch as diethyl ether, tetrahydrofuran and dioxane, in additioncarboxylic esters, such as ethyl acetate, moreover nitriles such asacetonitrile, and also strongly polar solvents such asdimethylformamide, dimethyl sulphoxide and sulpholane.

When carrying out process (G) according to the invention, the reactiontemperature can be varied within a substantial range. In general, thereaction temperature is between -20° C. and +100° C., preferably between0° C. and 50° C.

Process (G) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (G) according to the invention, the startingmaterials of the formulae (I-1-a) to (I-5-a) and the relevantchloroformic ester or chloroformic thioester of the formula (X) aregenerally used in each case in approximately equivalent amounts.However, it is also possible to employ one or the other component in alarger excess (up to 2 mol). Working-up is carried out by customarymethods. In general, a procedure is followed in which precipitated saltsare removed and the reaction mixture which remains is concentrated bystripping off the diluent.

Process (H) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are reacted in each casewith (Hα) compounds of the formula (XI) in the presence of a diluentand, if appropriate, in the presence of an acid binder, or (Hβ) carbondisulphide and subsequently with alkyl halides of the formula (XII), ifappropriate in the presence of a diluent and if appropriate in thepresence of a base.

In preparation process (Hα), approximately 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (XI) is reacted permole of starting compound of the formulae (I-1-a) to (I-5-a) at 0 to120° C., preferably at 20 to 60° C.

Suitable diluents which are optionally added are all inert polar organicsolvents such as ethers, amides, sulphones, sulphoxides, but alsohalogenoalkanes.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-5-a) is synthesized by adding strong deprotonating agents such as,for example, sodium hydride or potassium tertiary-butoxide, a furtheraddition of acid binders can be dispensed with.

If acid binders are employed, then suitable substances are customaryinorganic or organic bases, with sodium hydroxide, sodium carbonate,potassium carbonate, pyridine and triethylamine being mentioned by wayof example.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

In preparation process (Hβ), the equimolar amount, or an excess, ofcarbon disulphide is added in each case per mole of starting compoundsof the formulae (I-1-a) to (I-5-a). This process is preferably carriedout at temperatures from 0 to 50° C. and, in particular, at 20 to 30° C.

Frequently, it is expedient first to prepare the corresponding salt fromthe compounds of the formulae (I-1-a) to (I-5-a) by adding a base (suchas, for example, potassium tertiary butoxide or sodium hydride). Thecompounds (I-1-a) to (I-5-a) are reacted with carbon disulphide in eachcase until the formation of the intermediate is complete, for exampleafter stirring for several hours at room temperature.

Bases which can be employed in process (Hβ) are all customary protonacceptors. The following are preferably usable: alkali metal hydrides,alkali metal alkoxides, alkali metal carbonates, alkali metal hydrogencarbonates, alkaline earth metal carbonates, alkaline earth metalhydrogen carbonates, or nitrogen bases. Examples which may be mentionedare sodium hydride, sodium methoxide, sodium hydroxide, calciumhydroxide, potassium carbonate, sodium hydrogen carbonate,triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline,diazabicyclooctane (DABCO), diazabicyclononene (DBN) anddiazabicycloundecene (DBU).

Diluents which can be used in this process are all customary solvents.

The following may preferably be used: aromatic hydrocarbons such asbenzene or toluene, alcohols such as methanol, ethanol, isopropanol orethylene glycol, nitriles such as acetonitrile, ethers such astetrahydrofuran or dioxane, amides such as di-methylformamide, or otherpolar solvents such as dimethyl sulphoxide or sulpholane.

The further reaction with the alkyl halide of the formula (XII) ispreferably carried out at 0 to 70° C., in particular at 20 to 50° C. Atleast the equimolar amount of alkyl halide is employed.

The process is carried out under atmospheric pressure or under elevatedpressure, preferably under atmospheric pressure.

Again, working-up is carried out by customary methods.

Process (I) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are reacted in each casewith sulphonyl chlorides of the formula (XIII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In preparation process (I), approximately 1 mol of sulphonyl chloride ofthe formula (XIII) is reacted per mole of starting compound of theformulae (I-1-a) to (I-5-a) at -20 to 150° C., preferably at 0 to 70° C.

Process (I) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert polar organic solvents such as ethers,amides, ketones, carboxylic esters, nitriles, sulphones, sulphoxides orhalogenated hydrocarbons such as methylene chloride.

Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-5-a) is synthesized by adding strong deprotonating agents (suchas, for example, sodium hydride or potassium tertiary-butylate), afurther addition of acid binders can be dispensed with.

If acid binders are employed, then suitable substances are customaryinorganic or organic bases, with sodium hydroxide, sodium carbonate,potassium carbonate, pyridine and triethylamine being mentioned by wayof example.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

Process (J) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are reacted in each casewith phosphorus compounds of the formula (XIV), if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.

In preparation process (J), 1 to 2, preferably 1 to 1.3, mol of thephosphorus compound of the formula (XIV) are reacted at temperaturesbetween -40° C. and 150° C., preferably between -10 and 110° C., toobtain compounds of the formulae (I-1-e) to (I-5-e).

Process (J) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert polar organic solvents such as ethers,carboxylic esters, halogenated hydrocarbons, ketones, amides, nitrites,sulphones, sulphoxides and the like.

Substances which are preferably employed are acetonitrile, dimethylsulphoxide, tetrahydrofuran, dimethylformamide or methylene chloride.

Suitable acid binders which are optionally added are customary inorganicor organic bases such as hydroxides, carbonates or amines. Exampleswhich may be mentioned are sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods of organicchemistry. The end products are preferably purified by crystallization,chromatography or by so-called "incipient distillation", i.e. removal ofthe volatile components in vacuo.

Process (K) is characterized in that compounds of the formulae (I-1-a)to (I-5-a) are reacted in each case with metal hydroxides or metalalkoxides of the formula (XV), or amines of the formula (XVI), ifappropriate in the presence of a diluent.

Diluents which can be employed in process (K) according to the inventionare preferably ethers such as tetrahydrofuran, dioxane, diethyl ether,or else alcohols such as methanol, ethanol and isopropanol, but alsowater. Process (K) according to the invention is generally carried outunder atmospheric pressure. The reaction temperature is generallybetween -20° C. and 100° C., preferably between 0° C. and 50° C.

Process (L) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are reacted in each casewith (Lα) compounds of the formula (XVII), if appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or (Lβ) with compounds of the formula (XVIII), if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.

In preparation process (Lα), approximately 1 mol of isocyanate of theformula (XVII) is reacted at 0 to 100° C., preferably at 20 to 50° C.,per mole of starting compound of the formulae (I-1-a) to (I-5-a).

Process (Lα) is preferably carried out in the presence of a diluent.

Suitable diluents are all inert organic solvents such as aromatichydrocarbons, halogenated hydrocarbons, ethers, amides, nitrites,sulphones or sulphoxides.

If appropriate, catalysts can be added to accelerate the reaction. Veryadvantageous catalysts which can be employed are organotin compoundssuch as, for example, dibutyltin dilaurate.

The process is preferably carried out under atmospheric pressure.

In preparation process (Lβ), approximately 1 mol of carbamoyl chlorideof the formula (XVIII) is reacted per mole of starting compound of theformulae (I-1-a) to (I-5-a) at 0 to 150° C., preferably at 20 to 70° C.

Suitable diluents which are optionally added are all inert polar organicsolvents such as ethers, carboxylic esters, nitrites, ketones, amides,sulphones, sulphoxides or halogenated hydrocarbons.

Dimethyl sulphoxide, tetrahydrofuran, diemthylformamide or methylenechloride are preferably employed.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-5-a) is synthesized by adding strong deprotonating agents (suchas, for example, sodium hydride or potassium tertiary-butoxide), afurther addition of acid binders can be dispensed with.

If acid binders are employed, then suitable substances are customaryinorganic or organic bases, with sodium hydroxide, sodium carbonate,potassium carbonate, triethylamine and pyridine being mentioned by wayof example.

The reaction can be carried out under atmospheric pressure or underelevated pressure, it is preferably carried out under atmosphericpressure. Working-up is carried out by customary methods.

The active compounds are suitable for controlling animal pests,preferably arthropods and nematodes, particularly insects and arachnidsencountered in agriculture, in forests, in the protection of storedproducts and materials, and in the hygiene sector. They are activeagainst normally sensitive and resistant species and against all or somestages of development. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spec..

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp..

From the order of the Anoplura, for example, Phylloxera vastatrix,Pemphigus, spp., Pediculus humanus corporis, Haematopinus spp. andLinognathus spp..

From the order of the Mallophaga, for example, Trichodectes spp. andDamalinea spp..

From the order of the Thysanoptera, for example, Hercinothrips femoralisand Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosomalanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp.,Phorodon humuli, Rhopalosiphura padi, Empoasca spp., Euscelis bilobatus,Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphaxstriatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotushederae, Pseudococcus spp. and Psylla spp..

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp..

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of the Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychusspp..

The active compounds according to the invention are distinguished by apotent insecticidal and acaricidal activity.

They can be employed particularly successfully for controllingphytopathogenic insects, such as, for example, against the larvae of themustard beetle (Phaedon cochleariae) or against the larvae of the greenrice leafhopper (Nephotettix cincticeps) or against the caterpillars ofthe diamond-back moth (Plutella maculipennis).

The active compounds according to the invention can furthermore be usedas defoliants, desiccants, haulm killers and, especially, asweedkillers. By weeds, in the broadest sense, these are to be understoodall plants which grow in locations where they are undesired. Whether thesubstances according to the invention act as total or selectiveherbicides depends essentially on the amount used.

The dosage rates of the active compounds according to the invention,required for controlling weeds, are between 0.001 and 10 kg/ha,preferably between 0.005 and 5 kg/ha.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochonra, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

Depending on the concentration, the compounds are suitable for totalweed control, for example on industrial terrain and rail tracks, and onpaths and areas with or without tree stands. Equally, the compounds canbe employed for controlling weeds in perennial crops, for exampleforests, ornamental tree plantings, orchards, vineyards, citrus groves,nut orchards, banana plantations, coffee plantations, tea plantations,rubber plantations, oil palm plantations, cocoa plantations, soft fruitplantings and hopfields, in lawns, turf and pastures, and for selectiveweed control in annual crops.

The active compounds according to the invention are highly suitable forthe selective control of monocotyledonous weeds in dicotyledonous cropspre- and post-emergence. For example, they can be employed verysuccessfully for controlling grass weeds in cotton or sugar beet.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspoemulsion concentrates,natural and synthetic materials impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If water is used as an extender, organic solvents can, for example, alsobe used as auxiliary solvents. Liquid solvents which are mainly suitableare: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, mineral andvegetable oils, alcohols such as butanol or glycol and their ethers andesters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as highly disperse silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample non-ionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latexes such as gum arabic,polyvinyl alcohol and polyvinyl acetate, or else natural phospholipidssuch as cephalins and lecithins, and synthetic phospholipids can be usedin the formulations. Further additives can be mineral and vegetableoils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilants, acaricides, nematicides,fungicides, growth regulators or herbicides. The insecticides include,for example, phosphoric esters, carbamates, carboxylic esters,chlorinated hydrocarbons, phenylureas, substances produced bymicroorganisms, and the like.

Examples of particularly advantageous components and mixtures are thefollowing:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-di-chloro-N-(4-trifluoromethylbenzyl)benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate, calciumpolysulphide, captafol, captan, carbendazim, carboxin, quinomethionate,chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb,cymoxanil, cyproconazole, cyprofuram, dichlorophen, diclobutrazol,diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole,dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine,dipyrithion, ditalimfos, dithianon, dodine, drazoxolon, edifenphos,epoxyconazole, ethirimol, etridiazole, fenarimol, fenbuconazole,fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentinacetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil,fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole,furalaxyl, furmecyclox, guazatine, hexachlorobenzene, hexaconazole,hymexazol, imazalil, imibenconazole, iminoctadine, iprobenfos (IBP),iprodione, isoprothiolane, kasugamycin, copper preparations such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture, mancopper,mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole,methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil, nickeldimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace,oxadixyl, oxamocarb, oxycarboxin, pefurazoate, penconazole, pencycuron,phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin,probenazole, prochloraz, procymidone, propamocarb, propiconazole,propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quintozene(PCNB), sulphur and sulphur preparations, tebuconazole, tecloftalam,tecnazene, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl,thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol,triazoxide, trichlarnide, tricyclazole, tridemorph, triflumizole,triforine, triticonazole, validamycin A, vinclozolin, zineb, ziram.

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furanecarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalarn, copper sulphate and othercopper preparations

Insecticides/Acaricides/Nematicides

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin, Bacillus thuringiensis, bendiocarb,benfuracarb, bensultap, beta-cyfluthrin, bifenthrin, BPMC, brofenprox,bromophos A, bufencarb, buprofezin, butocarboxin, butylpyridaben,cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cylhalothrin, cyhexatin, cypermethrin, cyromazine,deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dirmethoate, dimethylvinphos, dioxathion, disulfoton,edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos, fenamiphos, fenazaquin, fenbutatin oxide,fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin,fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam,flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate,fonophos, formnothion, fosthiazate, fubfenprox, furathiocarb, HCH,heptenophos, hexaflumuron, hexythiazox, imidacloprid, iprobenfos,isazophos, isofenphos, isoprocarb, isoxathion, ivermectin,lambda-cyhalothrin, lufenuron, malathion, mecarbam, mevinphos,mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion,methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,naled, NC 184, NI 25, nitenpyram, omethoate, oxamyl, oxydemethon M,oxydeprofos, parathion A, parathion M, permethrin, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M,pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos,prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin,pyrethrum, pyridaben, pyrimidifen, pyriproxifen, quinalphos, RH 5992,salithion, sebufos, silafluofen, sulfotep, sulprofos, tebufenozid,tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos,terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox,thiomethon, thionazin, thuringiensin, tralomethrin, triarathen,triazophos, triazuron, trichlorfon, triflumuron, trimethacarb,vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Herbicides

for example anilides such as, for example, diflufenican and propanil;arylcarboxylic acids such as, for example, dichloropicolinic acid,dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4-D,2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones such as, for example, chloridazon andnorflurazon; carbamates such as, for example, chlorpropham, desmedipham,phenmedipham and propham; chloroacetanilides such as, for example,alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlorand propachlor; dinitroanilines such as, for example, oryzalin,pendimethalin and trifluralin; diphenyl ethers such as, for example,acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen andoxyfluorfen; ureas such as, for example, chlortoluron, diuron,fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylaminessuch as, for example, alloxydim, clethodim, cycloxydim, sethoxydim andtralkoxydim; imidazolinones such as, for example, imazethapyr,imazamethabenz, imazapyr and imazaquin; nitriles such as, for example,bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example,mefenacet; sulfonylureas such as, for example, amido-sulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiocarbamates such as, for example, butylate, cycloate, di-allate,EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate;triazines such as, for example, atrazine, cyanazine, simazine, simetryn,terbutryn and terbutylazine; triazinones such as, for example,hexazinone, metamitron and metribuzin; others such as, for example,aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

The active compound according to the invention can furthermore bepresent in commercially available formulations and in the use forms,prepared from these formulations, as a mixture with synergists.Synergists are compounds which increase the action of the activecompounds, without it being necessary for the synergist added to beactive itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide ranges. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably from 0.0001 to 1% byweight.

They are used in a customary manner appropriate for the use forms.

When used against hygiene and stored-product pests, the active compoundis distinguished by an outstanding residual action on wood and clay andby a good stability to alkali on limed substrates.

The active compounds according to the invention act not only againstplant, hygiene and stored-product pests but also, in the veterinarymedicine sector, against parasitic animals (ectoparasites) such as hardticks, soft ticks, mange mites, Trombidae, flies (stinging and sucking),parasitic fly larvae, lice, hair lice, bird lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp..

From the order of the Mallophagida and the sub-orders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp..

From the order Diptera and the sub-orders Nematocerina and Brachycerina,for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp.,EusimuliurrL spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma, spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp..

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp..

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp..

From the sub-class of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Omithodorus spp., Otabiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemaphysatis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp..

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp..

For example, they show outstanding activity against Boophilus microplusand Lucilia cuprina.

The active compounds according to the invention are also suitable forcontrolling arthropods which attack agricultural livestock such as, forexample, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes,rabbits, chickens, turkeys, ducks, geese, bees, other domestic animalssuch as, for example, dogs, cats, cage birds, aquarium fish, andso-called laboratory animals, such as, for example, hamsters, guineapigs, rats and mice. By controlling these arthropods, it is intended todiminish cases of death and reductions in productivity (meat, milk,wool, hides, eggs, honey and the like), so that simpler and moreeconomical animal keeping is possible by employing the active compoundsaccording to the invention.

In the veterinary sector, the active compounds according to theinvention are used in a known manner by enteral administration in theform of, for example, tablets, capsules, drinks, drenches, granules,pastes, boluses, the feed-through method, suppositories, by parenteraladministration such as, for example, by injections (intramuscular,subcutaneous, intravenous, intraperitonial and the like), implants, bynasal administration, by dermal use in the form of, for example, bathingor dipping, spraying, pouring-on and spotting-on, washing, dusting, andwith the aid of moulded articles comprising active compound, such ascollars, ear marks, tail marks, limb bands, halters, marking devices andthe like.

When used for livestock, poultry, domestic animals and the like, theactive compounds of the formula (I) can be applied as formulations (forexample powders, emulsions, flowables) which comprise the activecompounds in an amount of 1 to 80% by weight, either directly or afterdilution by a factor of 100 to 10,000, or they may be used as a chemicalbath.

Moreover, it has been found that the compounds of the formula (I)according to the invention have a potent insecticidal activity againstinsects which destroy industrial materials.

The following insects may be mentioned by way of example and as beingpreferred, but without limitation:

Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendronspec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec., Dinoderus minutus.

Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur.

Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus.

Bristletails, such as Lepisma saccharina.

Industrial materials are to be understood as meaning, in the presentcontext, non-live materials such as, preferably, synthetic materials,glues, sizes, paper and board, leather, wood and derived timberproducts, and paints.

The material to be protected against attack by insects is veryparticularly preferably wood and derived timber products.

Wood and derived timber products which can be protected by the agentaccording to the invention, or by compositions comprising it, are to beunderstood as meaning, for example,: construction timber, wooden beams,railway sleepers, bridge components, jetties, wooden vehicles, boxes,pallets, containers, telephone poles, wood laggings, windows and doorsmade of wood, plywood, particle board, joiner's work, or wood productswhich, quite generally, are used in construction or in joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations such as powders, granules, solutions,suspensions, emulsions or pastes.

The abovementioned formulations can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if appropriate siccatives and UV stabilizers and, ifappropriate, colorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for the protection ofwood and derived timber products comprise the active compound accordingto the invention, in a concentration of 0.0001 to 95% by weight, inparticular 0.001 to 60% by weight.

The amount of the agents or concentrates employed depends on the speciesand the abundance of the insects and on the medium. The optimum amountused can be determined in each case by test series. However, in generalit suffices to employ 0.0001 to 20% by weight, preferably 0.001 to 10%by weight, of the active compound based on the material to be protected.

The solvent and/or diluent used is an organochemical solvent or solventmixture and/or an oily or oil-like organochemical solvent or solventmixture of low volatility and/or a polar organochemical solvent orsolvent mixture and/or water and, if appropriate, an emulsifier and/orwetting agent.

The organochemical solvents employed are preferably oily or oil-likesolvents with an evaporation number of above 35 and a flashpoint ofabove 30° C., preferably above 45° C. Substances which are used as suchoily and oil-type solvents of low volatility which are insoluble inwater are suitable mineral oils or their aromatic fractions ormineral-oil-comprising solvent mixtures, preferably white spirit,petroleum and/or alkylbenzene.

It is advantageous to use mineral oils with a boiling range of 170 to220° C., white spirit with a boiling range of 170 to 220° C., spindleoil with a boiling range of 250 to 350° C., petroleum or aromatics of aboiling range of 160 to 280° C., spirit of turpentine, and the like.

In a preferred embodiment, the substances used are liquid aliphatichydrocarbons with a boiling range of 180 to 210° C. or high-boilingmixtures of aromatic and aliphatic hydrocarbons with a boiling range of180 to 220° C. and/or spindle oil and/or monochloronaphthalene,preferably α-monochloronaphthalene.

The organic oily or oil-type solvents of low volatility with anevaporation number of above 35 and a flashpoint of above 30° C.,preferably above 45° C., can be replaced in part by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flashpoint ofabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

In a preferred embodiment, part of the organochemical solvent or solventmixture is replaced by an aliphatic polar organochemical solvent orsolvent mixture. Substances which are preferably used are aliphaticorganochemical solvents containing hydroxyl and/or ester and/or ethergroups, such as, for example, glycol ethers, esters and the like.

Organochemical binders which are used within the scope of the presentinvention are the binding drying oils and/or synthetic resins which areknown per se, can be diluted with water, and/or are soluble, dispersibleor emulsifiable in the organochemical solvents employed, in particularbinders composed of, or comprising, an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenol resin, hydrocarbon resin, such as indene-coumarone resin,silicone resin, drying vegetable and/or drying oils and/or physicallydrying binders based on natural and/or synthetic resin.

The synthetic resin used as binder can be employed in the form of anemulsion, dispersion or solution. Substances which can also be used asbinders are bitumen or bitumenous substances in amounts of up to 10% byweight. In addition, colorants, pigments, water repellants, odoriferoussubstances and inhibitors or anti-corrosives and the like, all of whichare known per se, can be employed.

The composition or concentrate preferably comprises, in accordance withthe invention, at least one alkyd resin or modified alkyd resin and/or adrying vegetable oil as the organochemical binder. Substances which arepreferably used according to the invention are alkyd resins with an oilcontent of over 45% by weight, preferably 50 to 68% by weight.

All or some of the abovementioned binder can be replaced by a fixative(mixture) or a plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds or crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as di-butyl phthalate, dioctyl phthalate or benzylbutyl phthalate,phosphoric esters, such as tributyl phosphate, adipic esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers orhigher-molecular-weight glycol ethers, glycerol esters andp-toluenesulphonic esters.

Fixatives are based chemically on polyvinyl alkyl ethers such as, forexample, polyvinyl methyl ether, or ketones such as benzophenone orethylenebenzophenone.

Another suitable solvent or diluent is, in particular, water, ifappropriate in a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

A particularly effective protection of wood is achieved by means ofindustrial-scale impregnating processes, for example vacuum,double-vacuum or pressure processes.

If appropriate, the ready-to-use compositions can comprise otherinsecticides and, if appropriate, one or more fungicides.

Additional components which may be admixed are preferably theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are expressly part of the presentapplication.

Components which may very particularly preferably be admixed areinsecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and fungicides such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl butylcarbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

Preparation and use of the active compounds according to the inventioncan be seen from the examples which follow.

Preparation Examples Example (I-B-1-a-1) ##STR133##

11.3 g of the compound of Example (II-B-1) in 22 ml of DMF are addeddropwise at 0 to 10° C. to 8.82 g (0.075 mol) of potassium tert-butylatein 30 ml of DMF, and the mixture is stirred at room temperature. Theprogress of the reaction is monitored by means of thin-layerchromatography (TLC). When the reaction has ended, 250 ml of ice-waterare added, the mixture is acidified with concentrated hydrochloric acidat 0 to 10° C. until the pH is 2 and subjected to filtration withsuction, and the filtrate is washed with water, dried and brought to theboil with methyl tert-butyl ether (MTB ether)/n-hexane for purification.

Yield 7.90 g (77% of theory), m.p. >220° C.

The following compounds of the formula (I-1-a) were obtained analogouslyto Example I-B-1-a-1, or following the general information given for thepreparation of the compounds of the formula (I-1-a):

                                      TABLE 40                                    __________________________________________________________________________                                           (I-1-a) #                                 -                                                                          Ex. No.                                                                            V.sup.1                                                                           V.sup.2                                                                         V.sup.3                                                                           W Z.sub.n                                                                         A      B       Isomer                                                                            M.p. ° C.                        __________________________________________________________________________    I-B-1-a-2                                                                          C--Cl                                                                             N C--Cl                                                                             H H CH.sub.3                                                                             CH.sub.3                                                                              --  >220                                    1-B-1-a-3                                                                          C--Cl                                                                             N C--Cl                                                                             H H --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.2 --                                        β                                                                            >220                                      I-B-1-a-4 C--H N C--Cl Cl H --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2)                                          .sub.2 -- β >220                     I-B-1-a-5 C--Cl N C--Cl H H --(CH.sub.2).sub.2 --CHOCH.sub.3 --(CH.sub.2                                          ).sub.2 -- β >220                  __________________________________________________________________________

Example (I-B-1-1) ##STR135##

1.3 ml (0.012 mol) of isobutyryl chloride in 5 ml of anhydrous ethylacetate are added dropwise at reflux temperature to 2.34 g of thecompound of Example (I-B-1-a1) and 1.7 ml (12 mmol) of triethylamine in50 ml of anhydrous ethyl acetate, the mixture is stirred under reflux,and the progress of the reaction is monitored by means of TLC. After thereaction has ended, the mixture is concentrated, taken up in methylenechloride, washed twice with 50 ml of 0.5 N NaOH, dried and concentrated.The residue is recrystallized from MTB ether/n-hexane.

Yield 1.5 g (51% of theory), m.p. 204° C.

The following compounds of the formula (I-1-b) were obtained analogouslyto Example I-B-1-b-1, or following the general information given for thepreparation:

                                      TABLE 41                                    __________________________________________________________________________                                                  (I-1-b) #                          -                                                                          Ex. No.                                                                            V.sup.1                                                                           V.sup.2                                                                         V.sup.3                                                                           W Z.sub.n                                                                         A      B      R.sup.1 Isomer                                                                            M.p. ° C.                 __________________________________________________________________________    I-B-1-b-2                                                                          C--Cl                                                                             N C--Cl                                                                             H H CH.sub.3                                                                             CH.sub.3                                                                             i-C.sub.3 H.sub.7                                                                     --  149                                I-B-1-b-3 C--Cl N C--Cl H H CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 --O--CH.su                                                 b.2 -- 118                       I-B-1-b-4                                                                          C--Cl                                                                             N C--Cl                                                                             H H --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.2 --                                       i-C.sub.3 H.sub.7                                                                     β                                                                            204                                I-B-1-b-5 C--Cl N C--Cl H H --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2)                                                 .sub.2 -- C.sub.2 H.sub.5                                                     --O--CH.sub.2 β 190                                                       I-B-1-b-6 C--Cl N C--Cl H H                                                  --(CH.sub.2).sub.2 --CHCH.sub                                                 .3 --(CH.sub.2).sub.2 --                                                      4-Cl-Phenyl β 232                                                         I-B-1-b-7 C--Cl N C--Cl H H                                                  --(CH.sub.2).sub.2 --CHCH.sub                                                 .3 --(CH.sub.2).sub.2 --                                                      2-Thienyl β >220            __________________________________________________________________________

Example (I-B-1-c-1) ##STR137##

0.8 ml (0.008 mol) of ethyl chloroformate in 5 ml of anhydrous methylenechloride are added dropwise at 0 to 10° C. to 2.34 g of the compound ofExample (I-B-1-a-1) and 1.2 ml (0.008 mol) of triethylamine in 50 ml ofanhydrous methylene chloride. The mixture is stirred at room temperatureand the progress of the reaction is monitored by means of TLC. After thereaction has ended, the mixture is washed twice with 50 ml of 0.5 NNaOH, dried and concentrated, and the residue is recrystallized from MTBether/n-hexane. To purify the product further, it is boiled again inethyl acetate.

Yield 1.6 g (54% of theory), m.p. 208° C.

The following compounds of the formula (I-1-c) were obtained analogouslyto Example I-B-1-c-1, or following the general information given for thepreparation:

                                      TABLE 42                                    __________________________________________________________________________                                                   (I-1-c) #                         -                                                                          Ex. No.                                                                            V.sup.1                                                                           V.sup.2                                                                         V.sup.3                                                                           W Z.sub.n                                                                         A      B      L M R.sup.2                                                                          M.p. ° C.                                                                   Isomer                           __________________________________________________________________________    I-B-1-c-2                                                                          C--Cl                                                                             N C--Cl                                                                             H H CH.sub.3                                                                             CH.sub.3                                                                             O O C.sub.2 H.sub.5                                                                  104  --                               I-B-1-c-3                                                                          C--Cl                                                                             N C--Cl                                                                             H H --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.2 --                                       O O C.sub.2 H.sub.5                                                                  >220 β                           __________________________________________________________________________

Example (II-B-1) ##STR139##

9.5 g of methyl cis-4-methyl-1-amino-cyclohexanecarboxylatehydrochloride and 12.8 ml of triethylamine are stirred for 5 minutes in90 ml of anhydrous tetrahydrofuran (THF). After 7.8 g of3-(2-chloro)-pyridylacetic acid have been added in accordance withExample (XXIII-B-1), the mixture is stirred for a further 15 minutes atroom temperature, 17.8 ml (0.127 mol) of triethylamine are then added,and 4.3 ml of phosphorus oxychloride are immediately added in such a waythat the solution is at a moderate boil. The mixture is then refluxedfor 30 minutes. The mixture is poured into 400 ml of ice-water andextracted with methylene chloride, and the methylene chloride phase isdried and concentrated. The residue is purified by column chromatographyon silica gel (eluent methylene chloride/ethyl acetate 3:1).

Yield 11.3 g (76% of theory), m.p. 124° C.

The following compounds of the formula (II) were obtained analogously toExample II-B-I, or following the general information given for thepreparation:

                                      TABLE 43                                    __________________________________________________________________________                                                    (II) 40##                        -                                                                          Ex. No.                                                                            V.sup.1                                                                           V.sup.2                                                                         V.sup.3                                                                           W Z.sub.n                                                                         A      B       R.sup.8 M.p. ° C.                                                                   Isomer                         __________________________________________________________________________    II-B-2                                                                             C-Cl                                                                              N C--Cl                                                                             H H --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.2 --                                        CH.sub.3                                                                              146  β                         II-B-3                                                                             C--Cl                                                                             N C--Cl                                                                             H H CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                              138  --                             II-B-4                                                                             C--Cl                                                                             N C--Cl                                                                             H H --(CH.sub.2).sub.2 --CHOCH.sub.3 --(CH.sub.2).sub.2 --                                       CH.sub.3                                                                              122  β                           II-B-5 CH N C--Cl Cl H --(CH.sub.2).sub.2 --CHCH.sub.3 --(CH.sub.2).sub.                                                   2 -- CH.sub.3 136 β       II-B-6                                                                             CH  N C--Cl                                                                             Cl                                                                              H CH.sub.3                                                                             CH.sub.3                                                                              CH.sub.3                                                                              119  --                             II-B-7                                                                             CH  N C--Cl                                                                             Cl                                                                              H --(CH.sub.2).sub.2 --CHOCH.sub.3 --(CH.sub.2).sub.2 --                                       CH.sub.3                                                                              137  β                         __________________________________________________________________________

Example (XXV-B-1) ##STR141##

600 g (6.05 mol) of 1,1-dichloroethylene are added at room temperaturein the course of 5 minutes to 50 g (0.39 mol) of3-amino-2-chloropyridine in 120 ml of anhydrous acetonitrile, andstirring is continued for 5 minutes. 62.9 g (0.47 mol) of anhydrousCuCl₂ are subsequently rapidly added with cooling, 70.8 g of isopentylnitrite in 240 ml of acetonitrile are then added dropwise at roomtemperature in the course of 5 minutes, and the mixture is subsequentlystirred at room temperature until the evolution of gas has ceased. Themixture is then poured into 1600 ml of ice-cold 20% strength HCl andextracted repeatedly with methyl tert-butyl ether (MTB), and the organicphase is washed with 20% strength HCl, dried and concentrated.

Yield 165 g. The crude product is employed without further purificationfor the synthesis of the compound of Example (XXV-B-1).

Example (XXV-B-1) ##STR142##

327 ml of 30% strength aqueous NaHCO₃ solution are added dropwise withcooling to 165 g of the crude compound of Example (XXV-B-1) in 150 ml ofanhydrous methanol. The mixture is stirred for 5 hours under reflux, 48ml of concentrated sulphuric acid are subsequently added dropwise atroom temperature, and stirring is continued for 1 hour under reflux.

Excess methanol is removed in vacuo, the residue is extracted withmethylene chloride, and the methylene chloride phase is dried andconcentrated. The residue is distilled.

Yield 13.1 g (18% of theory), b.p.: 110-115° C. at 0.150 mbar.

Example (XXIII-B-1) ##STR143##

A solution of 4 g (0.095 mol) of lithium hydroxide (purity 98%) in 133ml of water is added dropwise at room temperature to 13.1 g (0.077 mol)of the compound of Example (XXIV-B-1) (purity 90%) in 133 ml ofanhydrous THF, and the mixture is stirred for one day at thistemperature. The progress of the reaction is monitored by means of TLCand, if appropriate, more lithium hydroxide is added. The mixture isthen concentrated, 50 ml of water are added, and the mixture isextracted with MTB ether. The aqueous phase is then acidified with 3NHCl and re-extracted with MTB ether. The aqueous phase is brought to pH4-5. The product is filtered off with suction and dried.

Yield 7.6 g (51% of theory), m.p.: 197° C.

Example (XXIII-B-2) ##STR144##

This compound was prepared by the following equation: ##STR145##

Compound (2)

1060 g of acrylonitrile (1) and 1120 g of DABCO are stirred for 60 hoursat 70° C. The mixture is allowed to cool, 4 l of toluene and 5 l ofwater are added, and the organic phase is washed with 1 N HCl, dried andconcentrated. The residue is distilled over a film evaporator at 0.5mbar/150° C.

Yield: 380 g, b.p. 70 to 72° C./0.20 mbar.

Compound (3)

1113 g of chlorine are passed into a mixture of 500 g of compound (2),250 g of carbon tetrachloride and 5.8 g of benzoyl peroxide at 70° C.Every hour, a further 5.8 g of benzoyl peroxide are added. The mixtureis subsequently concentrated. The crude product is employed in thepreparation of the compound (4) without further purification.

Yield: 862 g (Δ 79% of theory)

Compound (4)

309.1 g of compound (3), 950 ml of acetic acid and 221.3 g 78% strengthsulphuric acid are refluxed for 2.5 hours. After cooling, the mixture isstirred into approx. 1800 ml of ice-water, stirred for 1.5 hours andfiltered with suction. The crude product is stirred 2 more times with ineach case 3.5 l of water, filtered off with suction, washed untilneutral and dried at 50° C.

Yield: 64.3%, m.p. 131 to 132° C.

Compound (5)

220 g of compound (4) are heated with 1.2 l of POCl₃ for 3 hours at 160°C. under nitrogen pressure of 5 bar. Excess POCl₃ is distilled off, andthe residue is stirred into ice, filtered with suction, washedthoroughly with water and dried at 40° C.

Yield: 68%, NMR (200 MHz, CDCl₃): δ=4.65 (s,2H, CH₂ --Cl), 7.32 (d,1H,pyrid. 3-H), 7.83 (d,1H, pyrid. 6-H)

Compound (6)

A solution of 106 g (0.5 mol) of compound (5) (purity 94.5%) in 100 mlof toluene is slowly added dropwise at 60 to 80° C. to a mixture of 31 g(0.64 mol) of NaCN and 1 g of Aliquat 336 in 50 ml of water, and themixture is stirred for 8 hours at 80° C. After 31 g of NaCN and 1 g ofAliquat 336 have been added, the mixture is stirred for a further 8hours at 80° C. After cooling, in each case 100 ml of water and tolueneare added, the organic phase is washed twice with in each case 300 ml ofsaturated aqueous NaCl solution, dried and concentrated, and the residueis distilled under a high vacuum.

Yield: 29%, m.p. 80 to 82° C.

Example (XXIII-B-2)

24.2 g (0.127 mol) of compound (6) are added at 80 to 90° C. to amixture of 119.3 ml of concentrated sulphuric acid and 141.3 ml ofwater, and the mixture is stirred for 2 hours under reflux. Aftercooling, the mixture is poured into 500 ml of ice-water, filtered withsuction, washed with ice-water until neutral and dried.

Yield: 74%, m.p. 134 to 135° C.

Example (XXIII-B-3) ##STR146##

This compound was prepared in accordance with the following equation:##STR147##

Compound (8)

249 g of diethyl acetonedicarboxylate (7), 233.4 g of acetic anhydrideand 164.4 g of triethyl orthoformate are stirred for 1 hour at 140° C.All components which are volatile at up to 120° C. are distilled off andthe mixture is cooled to room temperature. 450 ml of 25% strength NH₃are subsequently added and the precipitate is filtered off with suction.It is suspended in water. The suspension is brought to pH 1 withconcentrated HCl and filtered with suction, and the product is driedovernight. The crude product is boiled up in 1 l of toluene, filteredoff with suction and dried.

Yield: 107.5 g (51% of theory), m.p. 214° C.

Compound (9)

11.0 g of compound (8) are refluxed for 7 hours in 67 ml of POCl₃. Mostof the excess POCl₃ is distilled off, and the residue is poured ontoice-water. The mixture is brought to pH 5 by adding Na₂ CO₃ andextracted with methylene chloride, and the methylene chloride phase isdried, concentrated and distilled.

Yield: 8.3 g (63% of theory), b.p. 83° C./0.3 mbar.

Compound (10)

8.6 g of lithium aluminium hydride are added, a little at a time, in thecourse of approximately 1 hour at 5 to 10° C. to 66.02 g of compound (9)in 120 ml of dry tetrahydrofuran (THF), and the mixture is stirred foranother 2 hours at this temperature. Then, 250 ml of 3N HCl are addeddropwise at 5 to 8° C., and the reaction mixture is evaporated todryness. The mixture is extracted with CH₂ Cl₂, dried, concentrated andpurified by column chromatography with the eluent ethylacetate/cyclohexane 1/2.

Yield: 32.9 g (61% of theory), m.p. 83° C.

Compound (11)

0.94 g of compound (10) is boiled under reflux for 19 hours togetherwith 7 ml of POCl₃. After the excess POCl₃ has been distilled off, theresidue is poured onto ice, and the crude product is filtered off withsuction, washed with water and dried in the air.

Yield: 0.25 g (26% of theory), m.p. 53° C.

Compound (12)

9.8 g of KCN in 38 ml of water are added dropwise at room temperature to10.27 g of compound (11) and 0.9 g of tetrabutylammonium sulphate in 50ml of methylene chloride, and the mixture is stirred overnight at roomtemperature. The organic phase is then concentrated and the residue ischromatographed on silica gel using the eluent ethyl acetate/cyclohexane1/2.

Yield: 6.0 g (63% of theory), m.p. 56° C.

(XXIII-B-3)

1 g of compound (12) is refluxed for 2 hours in 4.8 ml of concentratedsulphuric acid and 5.7 ml of water. When cold, the mixture is pouredinto 20 ml of ice-water and filtered with suction, and the product iswashed to neutrality and dried.

Yield: 0.85 g (81% of theory), m.p. 145° C.

The compounds of Examples (XXIII-B-1), (XXIII-B-2) and (XXIII-B-3) maybe converted into the corresponding acid chlorides in a generally knownmanner, for example also in situ (see Example II-B-1):

Example (XX-B-1) ##STR148## Example (XX-B-2) ##STR149## Example (XX-B-3)##STR150## Example (I-B-2-a-1) ##STR151##

3.36 g (0.03 mol) of potassium tert-butoxide are added at 0 to 5° C. inthe course of approximately 5 minutes to 9.8 g (0.03 mol) of thecompound of Example (III-2) (purity 73%) in 60 ml of absolutedimethylformamide (DMF), and stirring is continued for 1 hour at thistemperature. The reaction mixture is then poured into 8 ml ofconcentrated HCl in 180 ml of ice-water and stirred for 30 minutes. Theproduct is filtered off with suction, washed with water and dried at 40°C.

Yield: 7.0 g, m.p. 241.5° C.

Example (I-B-2-a-2)

The following compound is obtained analogously to Example (I-B-2-a-1),or following the general information for the preparation of compounds ofthe formula (I-2-a): ##STR152##

M.p. 195 to 198° C.

Example (I-B-2-b-1) ##STR153##

1.18 g (0.0088 mol) of 2,2-dimethylbutanoyl chloride in 5 ml ofmethylene chloride are added dropwise at 10 to 15° C. to 2.24 g (0.008mol) of the compound of Example (I-B-2-a-1) and 1.0 g (0.01 mol) oftriethylamine in 30 ml of methylene chloride, and the mixture is stirredovernight without cooling. 30 ml of methylene chloride are added, andthe mixture is washed in succession with 50 ml of water, 50 ml of 10%strength aqueous sodium carbonate solution and 2 portions of 50 ml ofwater, dried and concentrated. The residue is stirred in petroleumether, filtered off with suction and dried.

Yield: 1.2 g, m.p. 110° C.

Example (III-1) ##STR154##

5.38 g of the compound of Example (XX-B-2) and 4.13 g of ethyl1-hydroxycyclohexylcarboxylate are heated at 140° C. for a total of 14hours, and the mixture is concentrated and degassed using an oil pump.

Yield: 8.3 g, oil.

Without further characterization, the product was converted into thecompound of Example (I-B-2-a-2).

Example (III-2)

The compound ##STR155## which was also converted directly into thecompound of Example (I-B-2-a-1) without further characterization, wasobtained analogously to Example (III-1), or following the generalinformation given for the preparation of compounds of the formula (III).

USE EXAMPLES Example 1

Tetranychus test (OP resistant/spray treatment)

Solvent: 3 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentrations.

Bean plants (Phaseolus vulgaris) which are severely infested with alldevelopment stages of the greenhouse red spider mite or two-spottedspider mite (Tetranychus urticae) are sprayed with an active compoundpreparation of the desired concentration.

After the desired period of time, the destruction in % is determined.100% means that all the spider mites have been killed; 0% means thatnone of the spider mites have been killed.

In this test, an activity of 100% was shown, after 13 days, for exampleby the compound of Preparation Example (I-B-1-a-1) at an exemplaryactive compound concentration of 1000 ppm.

Example 2

Nephotettix test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentrations.

Rice seedlings (Oryza sativa) are treated by being dipped into thepreparation of the active compound of the desired concentration andpopulated with the green rice leafhopper (Nephotettix cincticeps) whilethe leaves are still moist.

After the desired period of time, the destruction in % is determined.100% means that all the leafhoppers have been killed; 0% means that noneof the leafhoppers have been killed.

In this test, a destruction of 100% was caused, after 6 days, forexample by the compounds of Preparation Examples (I-B-1-a-1),(I-B-1-b-1) and (I-B-1-c-1) at an exemplary active compoundconcentration of 0.1%.

What is claimed is:
 1. A compound of the formula (I) ##STR156## whereinA) V¹ represents nitrogen andV² represents CH or C--Z and V³ representsCY or B) V¹ represents CX andV² represents nitrogen and V³ represents CYor C) V¹ represents CX andV² represents CH or C--Z and V³ representsnitrogenand wherein W represents hydrogen, cyano, nitro, halogen, alkyl,alkenyl, alkynyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy,halogenoalkenyloxy, or in each case unsubstituted or substituted phenyl,phenoxy, phenylthio, phenylalkoxy or phenylalkylthio, X representshydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkylthio,halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, cyano, nitro or ineach case unsubstituted or substituted phenyl, phenoxy, phenylthio,phenylalkyloxy or phenylalkylthio, Y represents hydrogen, halogen,alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, cyano or nitro,Z represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl,halogenoalkoxy, hydroxyl, cyano, nitro or in each case unsubstituted orsubstituted phenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or Y and Ztogether with the carbon atoms to which they are bonded represent anunsubstituted or substituted cycle which is uninterrupted or interruptedby hetero atoms, in which case n represents 1, or W and Z together withthe immediately adjacent carbon atoms to which they are bonded representan unsubstituted or substituted cycle which is uninterrupted orinterrupted by hetero atoms, in which case n represents 1, n represents0, 1 or, in the cases A) and C) 0, 1 or 2, wherein the substituents Zare identical or different when n=2, Het represents the group ##STR157##wherein A represents hydrogen, or represents alkyl, alkenyl,alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which isunsubstituted or substituted by halogen, or represents in each casesaturated or unsaturated and unsubstituted or substituted cycloalkyl orheterocyclyl, or represents aryl, arylalkyl or hetaryl, each of which isunsubstituted or substituted by halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, cyano or nitro, B represents hydrogen, alkyl oralkoxyalkyl, or A and B together with the carbon atom to which they arebonded represent a saturated or unsaturated, unsubstituted orsubstituted carbocycle or heterocycle, G represents hydrogen or isselected from the group consisting of ##STR158## wherein E represents ametal ion equivalent or an ammonium ion, L represents oxygen or sulfur,M represents oxygen or sulfur, R¹ represents alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, each of which isunsubstituted or substituted by halogen, or represents cycloalkyl orheterocyclyl, each of which is unsubstituted or substituted by halogen,alkyl or alkoxy, or represents in each case unsubstituted or substitutedphenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R²represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each of whichis unsubstituted or substituted by halogen, or represents in each caseunsubstituted or substituted cycloalkyl, phenyl or benzyl, R³, R⁴ and R⁵independently of one another represent alkyl, alkoxy, alkylamino,dialkylamino, alkylthio, alkenylthio or cycloalkylthio, each of which isunsubstituted or substituted by halogen, or represent in each caseunsubstituted or substituted phenyl, benzyl, phenoxy or phenylthio, R⁶and R⁷ independently of one another represent hydrogen, or representalkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, each of which isunsubstituted or substituted by halogen, or represent in each caseunsubstituted or substituted phenyl or benzyl, or together with the Natom to which they are bonded form an unsubstituted or substituted cyclewhich optionally contains oxygen or sulfur.
 2. A pesticide or aherbicide, comprising at least one compound of the formula (I) accordingto claim 1 and one or more extenders and/or surfactants.
 3. A method ofcontrolling pests or weeds, comprising the step of allowing a compoundof the formula (I) according to claim 1 to act on pests or weeds, and/ortheir environment.
 4. A process for preparing a pesticide or aherbicidal composition, comprising the step of mixing a compound of theformula (I) according to claim 1 with extenders and/or surfactants.
 5. Aprocess for preparing a compound of the formula (I-1-a) ##STR159##wherein A, B, W, V¹, V², V³, n and Z are as defined in claim 1,comprising the step of subjecting to an intramolecular condensationreaction a compound of the formula (II) ##STR160## wherein A, B, W, V¹,V², V³, n and Z are as defined above andR⁸ represents alkyl, in thepresence of a diluent and in the presence of a base.
 6. A compound ofthe formula (II) ##STR161## wherein A represents alkyl, alkenyl,alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which isunsubstituted or substituted by halogen, or represents in each casesaturated or unsaturated and unsubstituted or substituted cycloalkyl orheterocyclyl, or represents aryl, arylalkyl or hetaryl, each of which isunsubstituted or substituted by halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, cyano or nitro,B represents alkyl or alkoxyalkyl, or Aand B together with the carbon atom to which they are bonded represent asaturated or unsaturated, unsubstituted or substituted carbocycle orheterocycle, whereinA) V¹ represents nitrogen andV² represents CH orC--Z and V³ represents CY or B) V¹ represents CX andV² representsnitrogen and V³ represents CY or C) V¹ represents CX andV² represents CHor C--Z and V³ represents nitrogen and whereinW represents hydrogen,cyano, nitro, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkylthio,halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, or in each caseunsubstituted or substituted phenyl, phenoxy, phenylthio, phenylalkoxyor phenylalkylthio, X represents hydrogen, halogen, alkyl, alkenyl,alkynyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy,halogenoalkenyloxy, cyano, nitro or in each case unsubstituted orsubstituted phenyl, phenoxy, phenylthio, phenylalkyloxy orphenylalkylthio, Y represents hydrogen, halogen, alkyl, alkoxy,alkylthio, halogenoalkyl, halogenoalkoxy, cyano or nitro, Z representshalogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy,hydroxyl, cyano, nitro or in each case unsubstituted or substitutedphenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or 6-memberedhetarylthio, phenylalkyloxy or phenylalkylthio, or Y and Z together withthe carbon atoms to which they are bonded represent an unsubstituted orsubstituted cycle which is uninterrupted or interrupted by hetero atoms,in which case n represents 1, or W and Z together with the immediatelyadjacent carbon atoms to which they are bonded represent anunsubstituted or substituted cycle which is uninterrupted or interruptedby hetero atoms, in which case n represents 1, n represents 0, 1 or, inthe cases A) and C) 0, 1 or 2, wherein the substituents Z are identicalor different when n=2, and R⁸ represents alkyl.
 7. A compound of theformula (XXI) ##STR162## wherein A represents alkyl, alkenyl,alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which isunsubstituted or substituted by halogen, or represents in each casesaturated or unsaturated and unsubstituted or substituted cycloalkyl orheterocyclyl, or represents aryl, arylalkyl or hetaryl, each of which isunsubstituted or substituted by halogen, alkyl, halogenoalkyl, alkoxy,halogenoalkoxy, cyano or nitro,B represents alkyl or alkoxyalkyl, or Aand B together with the carbon atom to which they are bonded represent asaturated or unsaturated, unsubstituted or substituted carbocycle orheterocycle, whereinA) V¹ represents nitrogen andV² represents CH orC--Z and V³ represents CY or B) V¹ represents CX andV² representsnitrogen and V³ represents CY or C) V¹ represents CX andV² represents CHor C--Z and V³ represents nitrogen and wherein W represents hydrogen,cyano, nitro, halogens alkyl, alkenyl, alkynyl, alkoxy, alkylthio,halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, or in each caseunsubstituted or substituted phenyl, phenoxy, phenylthio, phenylalkoxyor phenylalkylthio, X represents hydrogen, halogen, alkyl, alkenyl,alkynyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy,halogenoalkenyloxy, cyano, nitro or in each case unsubstituted orsubstituted phenyl, phenoxy, phenylthio, phenylalkyloxy orphenylalkylthio, Y represents hydrogen, halogen, alkyl, alkoxy,alkylthio, halogenoalkyl, halogenoalkoxy, cyano or nitro, Z representshalogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy,hydroxyl, cyano, nitro or in each case unsubstituted or substitutedphenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or 6-memberedhetarylthio, phenylalkyloxy or phenylalkylthio, or Y and Z together withthe carbon atoms to which they are bonded represent an unsubstituted orsubstituted cycle which is uninterrupted or interrupted by hetero atoms,in which case n represents 1, or W and Z together with the immediatelyadjacent carbon atoms to which they are bonded represent anunsubstituted or substituted cycle which is uninterrupted or interruptedby hetero atoms, in which case n represents 1, n represents 0, 1 or, inthe cases A) and C) 0, 1 or 2, wherein the substituents Z are identicalor different when n=2.